U.S. patent application number 17/045204 was filed with the patent office on 2021-06-03 for weed control from applications of pyridine carboxylic acid herbicides and 4-hydroxyphenyl-pyruvate dioxygenase (hppd) inhibitors.
This patent application is currently assigned to Dow AgroSciences LLC. The applicant listed for this patent is Dow AgroSciences LLC. Invention is credited to Bryston L. Bangel, Norbert M. Satchivi, Paul R. Schmitzer.
Application Number | 20210161135 17/045204 |
Document ID | / |
Family ID | 1000005404949 |
Filed Date | 2021-06-03 |
United States Patent
Application |
20210161135 |
Kind Code |
A1 |
Satchivi; Norbert M. ; et
al. |
June 3, 2021 |
WEED CONTROL FROM APPLICATIONS OF PYRIDINE CARBOXYLIC ACID
HERBICIDES AND 4-HYDROXYPHENYL-PYRUVATE DIOXYGENASE (HPPD)
INHIBITORS
Abstract
Disclosed herein are herbicidal compositions containing a
herbicidally effective amount of (a) a pyridine carboxylic acid
herbicide or an agriculturally acceptable N-oxide, salt, or ester
thereof, and (b) a 4-hydroxyphenyl-pyruvate dioxygenase (HPPD)
inhibitor or an agriculturally acceptable salt or ester thereof.
Also disclosed herein are methods of controlling undesirable
vegetation which comprise applying to vegetation or an area
adjacent the vegetation or applying to soil or water to prevent the
emergence or growth of vegetation (a) a pyridine carboxylic acid
herbicide or an agriculturally acceptable N-oxide, salt, or ester
thereof and (b) a 4-hydroxyphenyl-pyruvate dioxygenase (HPPD)
inhibitor or an agriculturally acceptable salt or ester thereof,
wherein (a) and (b) are each applied in an amount sufficient to
provide a herbicidal effect.
Inventors: |
Satchivi; Norbert M.;
(Carmel, IN) ; Bangel; Bryston L.; (Mooresville,
IN) ; Schmitzer; Paul R.; (Indianapolis, IN) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
Dow AgroSciences LLC |
Indianapolis |
IN |
US |
|
|
Assignee: |
Dow AgroSciences LLC
Indianapolis
IN
|
Family ID: |
1000005404949 |
Appl. No.: |
17/045204 |
Filed: |
April 4, 2019 |
PCT Filed: |
April 4, 2019 |
PCT NO: |
PCT/US19/25699 |
371 Date: |
October 5, 2020 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
|
|
62652377 |
Apr 4, 2018 |
|
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Current U.S.
Class: |
1/1 |
Current CPC
Class: |
A01N 37/40 20130101;
A01N 41/10 20130101; A01N 43/56 20130101; A01N 43/40 20130101; A01N
43/80 20130101 |
International
Class: |
A01N 43/40 20060101
A01N043/40; A01N 43/56 20060101 A01N043/56; A01N 43/80 20060101
A01N043/80; A01N 41/10 20060101 A01N041/10; A01N 37/34 20060101
A01N037/34 |
Claims
1. A herbicidal composition comprising a herbicidally effective
amount of (a) a pyridine carboxylic acid herbicide or an
agriculturally acceptable N-oxide, salt, or ester thereof and (b) a
4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor or an
agriculturally acceptable salt thereof, wherein the pyridine
carboxylic acid herbicide comprises a compound defined by Formula
(I) ##STR00051## wherein X is N or CY, wherein Y is hydrogen,
halogen, C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 haloalkyl,
C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3
alkylthio or C.sub.1-C.sub.3 haloalkylthio; R.sup.1 is OR.sup.1' or
NR.sup.1''R.sup.1'', wherein R.sup.1' is hydrogen, C.sub.1-C.sub.8
alkyl, or C.sub.7-C.sub.10 arylalkyl, and R.sup.1'' and R.sup.1''
are independently hydrogen, C.sub.1-C.sub.12 alkyl,
C.sub.3-C.sub.12 alkenyl, or C.sub.3-C.sub.12 alkynyl; R.sup.2 is
halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, cyano, or a group of the formula
--CR.sup.17.dbd.CR.sup.18--SiR.sup.19R.sup.20R.sup.21, wherein
R.sup.17 is hydrogen, F, or Cl; R.sup.18 is hydrogen, F, Cl,
C.sub.1-C.sub.4 alkyl, or C.sub.1-C.sub.4 haloalkyl; and R.sup.19,
R.sup.20, and R.sup.21 are independently C.sub.1-C.sub.10 alkyl,
C.sub.3-C.sub.6 cycloalkyl, phenyl, substituted phenyl,
C.sub.1-C.sub.10 alkoxy, or OH; R.sup.3 and R.sup.4 are
independently hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6
haloalkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 haloalkenyl,
C.sub.3-C.sub.6 alkynyl, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl,
C.sub.1-C.sub.6 alkylcarbamyl, C.sub.1-C.sub.6 alkylsulfonyl,
C.sub.1-C.sub.6 trialkylsilyl, C.sub.1-C.sub.6 dialkylphosphonyl,
or R.sup.3 and R.sup.4 taken together with N is a 5- or 6-membered
saturated ring, or R.sup.3 and R.sup.4 taken together represent
.dbd.CR.sup.3'(R.sup.4'), wherein R.sup.3' and R.sup.4' are
independently hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.3-C.sub.6
alkenyl, C.sub.3-C.sub.6 alkynyl, C.sub.1-C.sub.6 alkoxy or
C.sub.1-C.sub.6 alkylamino, or, R.sup.3' and R.sup.4' taken
together with .dbd.C represent a 5- or 6-membered saturated ring; A
is one of groups A1 to A36 ##STR00052## ##STR00053## ##STR00054##
##STR00055## ##STR00056## ##STR00057## R.sup.5, if applicable to
the A group, is hydrogen, halogen, C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, cyclopropyl, halocyclopropyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3
haloalkoxy, C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, OH, or CN; R.sup.6, R.sup.6', and R.sup.6'', if
applicable to the A group, are independently hydrogen, halogen,
C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, cyclopropyl,
halocyclopropyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4
haloalkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy,
C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio,
C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino or
C.sub.2-C.sub.4 haloalkylamino, OH, CN, or NO.sub.2; R.sup.7 and
R.sup.7' are independently hydrogen, halogen, C.sub.1-C.sub.4
alkyl, C.sub.1-C.sub.4 haloalkyl, cyclopropyl, halocyclopropyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3
haloalkoxy, C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.1-C.sub.4
haloalkylamino, or phenyl; R.sup.8 is hydrogen, C.sub.1-C.sub.6
alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6 alkenyl,
C.sub.3-C.sub.6 haloalkenyl, C.sub.3-C.sub.6 alkynyl, formyl,
C.sub.1-C.sub.3 alkylcarbonyl, C.sub.1-C.sub.3 haloalkylcarbonyl,
C.sub.1-C.sub.6 alkoxycarbonyl, C.sub.1-C.sub.6 alkylcarbamyl,
C.sub.1-C.sub.6 alkylsulfonyl, C.sub.1-C.sub.6 trialkylsilyl, or
phenyl; or an agriculturally acceptable N-oxide or salt
thereof.
2. The composition of claim 1, wherein the pyridine carboxylic acid
herbicide comprises a compound defined by Formula (II) ##STR00058##
wherein R.sup.1 is OR.sup.1' or NR.sup.1''R.sup.1''', wherein
R.sup.1' is hydrogen, C.sub.1-C.sub.8 alkyl, or C.sub.7-C.sub.10
arylalkyl, and R.sup.1'' and R.sup.1''' are independently hydrogen,
C.sub.1-C.sub.12 alkyl, C.sub.3-C.sub.12 alkenyl, or
C.sub.3-C.sub.12 alkynyl; R.sup.2 is halogen, C.sub.1-C.sub.4
alkyl, C.sub.1-C.sub.4 haloalkyl, C.sub.2-C.sub.4 alkenyl,
C.sub.2-C.sub.4 haloalkenyl, C.sub.2-C.sub.4 alkynyl,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4
alkylthio, C.sub.1-C.sub.4 haloalkylthio, amino, C.sub.1-C.sub.4
alkylamino, C.sub.2-C.sub.4 haloalkylamino, formyl, C.sub.1-C.sub.3
alkylcarbonyl, C.sub.1-C.sub.3 haloalkylcarbonyl, cyano, or a group
of the formula
--CR.sup.17.dbd.CR.sup.18--SiR.sup.19R.sup.20R.sup.21, wherein
R.sup.17 is hydrogen, F, or Cl; R.sup.18 is hydrogen, F, Cl,
C.sub.1-C.sub.4 alkyl, or C.sub.1-C.sub.4 haloalkyl; and R.sup.19,
R.sup.20, and R.sup.21 are independently C.sub.1-C.sub.10 alkyl,
C.sub.3-C.sub.6 cycloalkyl, phenyl, substituted phenyl,
C.sub.1-C.sub.10 alkoxy, or OH; R.sup.3 and R.sup.4 are
independently hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6
haloalkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 haloalkenyl,
C.sub.3-C.sub.6 alkynyl, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl,
C.sub.1-C.sub.6 alkylcarbamyl, C.sub.1-C.sub.6 alkylsulfonyl,
C.sub.1-C.sub.6 dialkylphosphonyl, or R.sup.3 and R.sup.4 taken
together with N is a 5- or 6-membered saturated ring, or R.sup.3
and R.sup.4 taken together represent .dbd.CR.sup.3'(R.sup.4'),
wherein R.sup.3' and R.sup.4' are independently hydrogen,
C.sub.1-C.sub.6 alkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6
alkynyl, C.sub.1-C.sub.6 alkoxy or C.sub.1-C.sub.6 alkylamino, or,
R.sup.3' and R.sup.4' taken together with .dbd.C represent a 5- or
6-membered saturated ring; A is A1, A2, A3, A4, A5, A6, A7, A8, A9,
A10, A11, A12, A13, A14, A15, A16, A17, A18, A19, A20, A21, A22,
A23, A24, A25, A26, A27, A28, A29, A30, A31, A32, A33, A34, A35, or
A36; R.sup.5 is hydrogen, halogen, C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, cyclopropyl, halocyclopropyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3
haloalkoxy, C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, OH, or CN; R.sup.6, R.sup.6', and R.sup.6'' are
independently hydrogen, halogen, C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, cyclopropyl, halocyclopropyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3
haloalkoxy, C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino or C.sub.2-C.sub.4
haloalkylamino, OH, CN, or NO.sub.2; R.sup.7 and R.sup.7' are
independently hydrogen, halogen, C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, cyclopropyl, halocyclopropyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3
haloalkoxy, C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, or phenyl; and R.sup.8 is hydrogen, C.sub.1-C.sub.6
alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6 alkenyl,
C.sub.3-C.sub.6 haloalkenyl, C.sub.3-C.sub.6 alkynyl, formyl,
C.sub.1-C.sub.3 alkylcarbonyl, C.sub.1-C.sub.3 haloalkylcarbonyl,
C.sub.1-C.sub.6 alkoxycarbonyl, C.sub.1-C.sub.6 alkylcarbamyl,
C.sub.1-C.sub.6 alkylsulfonyl, C.sub.1-C.sub.6 trialkylsilyl, or
phenyl; or an agriculturally acceptable N-oxide or salt
thereof.
3. The composition of claim 2, wherein R.sup.1 is OR.sup.1',
wherein R.sup.1' is hydrogen, C.sub.1-C.sub.8 alkyl, or
C.sub.7-C.sub.10 arylalkyl; R.sup.2 is halogen, C.sub.1-C.sub.4
alkyl, C.sub.1-C.sub.4 haloalkyl, C.sub.2-C.sub.4-alkenyl,
C.sub.2-C.sub.4 haloalkenyl, C.sub.2-C.sub.4 alkynyl,
C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4
alkylthio, or C.sub.1-C.sub.4 haloalkylthio; R.sup.3 and R.sup.4
are hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl,
C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 haloalkenyl,
C.sub.3-C.sub.6 alkynyl, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, or R.sup.3 and R.sup.4 taken
together represent .dbd.CR.sup.3'(R.sup.4'), wherein R.sup.3' and
R.sup.4' are independently hydrogen, C.sub.1-C.sub.6 alkyl,
C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 alkynyl, C.sub.1-C.sub.6
alkoxy or C.sub.1-C.sub.6 alkylamino; A is A1, A2, A3, A7, A8, A9,
A10, A11, A12, A13, A14, A15, A21, A22, A23, A24, A27, A28, A29,
A30, A31, or A32; R.sup.5 is hydrogen, halogen, C.sub.1-C.sub.4
alkyl, C.sub.1-C.sub.4 haloalkyl, C.sub.2-C.sub.4 alkenyl,
C.sub.2-C.sub.4 haloalkenyl, C.sub.2-C.sub.4 alkynyl,
C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3
alkylthio, C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4
alkylamino, or C.sub.2-C.sub.4 haloalkylamino; R.sup.6, R.sup.6',
and R.sup.6'' are independently hydrogen, halogen, C.sub.1-C.sub.4
alkyl, C.sub.1-C.sub.4 haloalkyl, cyclopropyl, halocyclopropyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3
haloalkoxy, CN, or NO.sub.2; R.sup.7 and R.sup.7' are independently
hydrogen, halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
haloalkyl, C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3 haloalkoxy,
C.sub.1-C.sub.3 alkylthio, cyclopropyl, amino or C.sub.1-C.sub.4
alkylamino; and R.sup.8 is hydrogen, C.sub.1-C.sub.6 alkyl,
C.sub.1-C.sub.4 haloalkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6
haloalkenyl, formyl, C.sub.1-C.sub.3 alkylcarbonyl, C.sub.1-C.sub.3
haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl, or
C.sub.1-C.sub.6 alkylcarbamyl.
4. The composition of claim 1, wherein the pyridine carboxylic acid
herbicide comprises a compound defined by Formula (III):
##STR00059## wherein X is N or CY, wherein Y is hydrogen, halogen,
C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 haloalkyl, C.sub.1-C.sub.3
alkoxy, C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio or
C.sub.1-C.sub.3 haloalkylthio; R.sup.1 is OR.sup.1' or
NR.sup.1''R.sup.1''', wherein R.sup.1' is hydrogen, C.sub.1-C.sub.8
alkyl, or C.sub.7-C.sub.10 arylalkyl, and R.sup.1'' and R.sup.1''
are independently hydrogen, C.sub.1-C.sub.12 alkyl,
C.sub.3-C.sub.12 alkenyl, or C.sub.3-C.sub.12 alkynyl; R.sup.2 is
halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, cyano, or a group of the formula
--CR.sup.17.dbd.CR.sup.18--SiR.sup.19R.sup.20R.sup.21, wherein
R.sup.17 is hydrogen, F, or Cl; R.sup.18 is hydrogen, F, Cl,
C.sub.1-C.sub.4 alkyl, or C.sub.1-C.sub.4 haloalkyl; and R.sup.19,
R.sup.20, and R.sup.21 are independently C.sub.1-C.sub.10 alkyl,
C.sub.3-C.sub.6 cycloalkyl, phenyl, substituted phenyl,
C.sub.1-C.sub.10 alkoxy, or OH; R.sup.3 and R.sup.4 are
independently hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6
haloalkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 haloalkenyl,
C.sub.3-C.sub.6 alkynyl, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl,
C.sub.1-C.sub.6 alkylcarbamyl, C.sub.1-C.sub.6 alkylsulfonyl,
C.sub.1-C.sub.6 trialkylsilyl, C.sub.1-C.sub.6 dialkylphosphonyl,
or R.sup.3 and R.sup.4 taken together with N is a 5- or 6-membered
saturated ring, or R.sup.3 and R.sup.4 taken together represent
.dbd.CR.sup.3'(R.sup.4'), wherein R.sup.3' and R.sup.4' are
independently hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.3-C.sub.6
alkenyl, C.sub.3-C.sub.6 alkynyl, C.sub.1-C.sub.6 alkoxy or
C.sub.1-C.sub.6 alkylamino, or, R.sup.3' and R.sup.4' taken
together with .dbd.C represent a 5- or 6-membered saturated ring;
R.sup.6 and R.sup.6' are independently hydrogen, halogen,
C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, cyclopropyl,
halocyclopropyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4
haloalkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy,
C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio,
C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino or
C.sub.2-C.sub.4 haloalkylamino, OH, CN, or NO.sub.2; R.sup.7 and
R.sup.7' are independently hydrogen, halogen, C.sub.1-C.sub.4
alkyl, C.sub.1-C.sub.4 haloalkyl, cyclopropyl, halocyclopropyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3
haloalkoxy, C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, or phenyl; and R.sup.8 is hydrogen, C.sub.1-C.sub.6
alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6 alkenyl,
C.sub.3-C.sub.6 haloalkenyl, C.sub.3-C.sub.6 alkynyl, formyl,
C.sub.1-C.sub.3 alkylcarbonyl, C.sub.1-C.sub.3 haloalkylcarbonyl,
C.sub.1-C.sub.6 alkoxycarbonyl, C.sub.1-C.sub.6 alkylcarbamyl,
C.sub.1-C.sub.6 alkylsulfonyl, C.sub.1-C.sub.6 trialkylsilyl, or
phenyl; or an agriculturally acceptable N-oxide or salt
thereof.
5. The composition of claim 1, wherein the pyridine carboxylic acid
herbicide comprises one of the following: ##STR00060##
##STR00061##
6. The composition of claim 1, wherein the pyridine carboxylic acid
herbicide comprises ##STR00062##
7. The composition of claim 1, wherein (b) is a
4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor
herbicide.
8. The composition of claim 7, wherein the 4-hydroxyphenyl-pyruvate
dioxygenase (HPPD) inhibitor herbicide is selected from the group
consisting of benzobicyclon, benzofenap, bicyclopyrone,
fenquinotrione, isoxachlortole, isoxaflutole, mesotrione,
pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tembotrione,
tefuryltrione, topramezone, or an agriculturally acceptable salt
thereof, and combinations thereof.
9. The composition of claim 8, wherein the weight ratio of (a) to
(b) is within the range from about 1:8000 to about 1000:1.
10. The composition of claim 9, wherein the weight ratio of (a) to
(b) is within the range from about 1:500 to about 60:1.
11. The composition of claim 10, wherein the weight ratio of (a) to
(b) is within the range from about 1:30 to about 5:1.
12. The composition claim 1, further comprising an agriculturally
acceptable adjuvant or carrier.
13. The composition of claim 1, further comprising an additional
pesticide.
14. The composition of claim 1, wherein the active ingredients in
the composition consist of (a) and (b).
15. The composition of claim 1, wherein the composition is provided
as a herbicidal concentrate.
16. A method of controlling undesirable vegetation comprising
applying to vegetation or an area adjacent the vegetation or
applying to soil or water to control the emergence or growth of
vegetation a herbicidally effective amount of: (a) a pyridine
carboxylic acid herbicide comprising a compound defined by Formula
(I) ##STR00063## wherein X is N or CY, wherein Y is hydrogen,
halogen, C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 haloalkyl,
C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3
alkylthio or C.sub.1-C.sub.3 haloalkylthio; R.sup.1 is OR.sup.1' or
NR.sup.1''R.sup.1''', wherein R.sup.1' is hydrogen, C.sub.1-C.sub.8
alkyl, or C.sub.7-C.sub.10 arylalkyl, and R.sup.1'' and R.sup.1''
are independently hydrogen, C.sub.1-C.sub.12 alkyl,
C.sub.3-C.sub.12 alkenyl, or C.sub.3-C.sub.12 alkynyl; R.sup.2 is
halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, cyano, or a group of the formula
--CR.sup.17.dbd.CR.sup.18--SiR.sup.19R.sup.20R.sup.21, wherein
R.sup.17 is hydrogen, F, or Cl; R.sup.18 is hydrogen, F, Cl,
C.sub.1-C.sub.4 alkyl, or C.sub.1-C.sub.4 haloalkyl; and R.sup.19,
R.sup.20, and R.sup.21 are independently C.sub.1-C.sub.10 alkyl,
C.sub.3-C.sub.6 cycloalkyl, phenyl, substituted phenyl,
C.sub.1-C.sub.10 alkoxy, or OH; R.sup.3 and R.sup.4 are
independently hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6
haloalkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 haloalkenyl,
C.sub.3-C.sub.6 alkynyl, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl,
C.sub.1-C.sub.6 alkylcarbamyl, C.sub.1-C.sub.6 alkylsulfonyl,
C.sub.1-C.sub.6 trialkylsilyl, C.sub.1-C.sub.6 dialkylphosphonyl,
or R.sup.3 and R.sup.4 taken together with N is a 5- or 6-membered
saturated ring, or R.sup.3 and R.sup.4 taken together represent
.dbd.CR.sup.3'(R.sup.4'), wherein R.sup.3' and R.sup.4' are
independently hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.3-C.sub.6
alkenyl, C.sub.3-C.sub.6 alkynyl, C.sub.1-C.sub.6 alkoxy or
C.sub.1-C.sub.6 alkylamino, or, R.sup.3' and R.sup.4' taken
together with .dbd.C represent a 5- or 6-membered saturated ring; A
is one of groups A1 to A36 ##STR00064## ##STR00065## ##STR00066##
##STR00067## ##STR00068## ##STR00069## R.sup.5, if applicable to
the A group, is hydrogen, halogen, C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, cyclopropyl, halocyclopropyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3
haloalkoxy, C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, OH, or CN; R.sup.6, R.sup.6', and R.sup.6'', if
applicable to the A group, are independently hydrogen, halogen,
C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, cyclopropyl,
halocyclopropyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4
haloalkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy,
C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio,
C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino or
C.sub.2-C.sub.4 haloalkylamino, OH, CN, or NO.sub.2; R.sup.7 and
R.sup.7' are independently hydrogen, halogen, C.sub.1-C.sub.4
alkyl, C.sub.1-C.sub.4 haloalkyl, cyclopropyl, halocyclopropyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3
haloalkoxy, C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.1-C.sub.4
haloalkylamino, or phenyl; R.sup.8 is hydrogen, C.sub.1-C.sub.6
alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6 alkenyl,
C.sub.3-C.sub.6 haloalkenyl, C.sub.3-C.sub.6 alkynyl, formyl,
C.sub.1-C.sub.3 alkylcarbonyl, C.sub.1-C.sub.3 haloalkylcarbonyl,
C.sub.1-C.sub.6 alkoxycarbonyl, C.sub.1-C.sub.6 alkylcarbamyl,
C.sub.1-C.sub.6 alkylsulfonyl, C.sub.1-C.sub.6 trialkylsilyl, or
phenyl; or an agriculturally acceptable N-oxide or salt thereof;
and (b) a 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor or
an agriculturally acceptable salt thereof.
17. The method of claim 16, wherein the pyridine carboxylic acid
herbicide comprises a compound defined by Formula (II) ##STR00070##
wherein R.sup.1 is OR.sup.1' or NR.sup.1''R.sup.1''', wherein
R.sup.1' is hydrogen, C.sub.1-C.sub.8 alkyl, or C.sub.7-C.sub.10
arylalkyl, and R.sup.1'' and R.sup.1''' are independently hydrogen,
C.sub.1-C.sub.12 alkyl, C.sub.3-C.sub.12 alkenyl, or
C.sub.3-C.sub.12 alkynyl; R.sup.2 is halogen, C.sub.1-C.sub.4
alkyl, C.sub.1-C.sub.4 haloalkyl, C.sub.2-C.sub.4 alkenyl,
C.sub.2-C.sub.4 haloalkenyl, C.sub.2-C.sub.4 alkynyl,
C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4
alkylthio, C.sub.1-C.sub.4 haloalkylthio, amino, C.sub.1-C.sub.4
alkylamino, C.sub.2-C.sub.4 haloalkylamino, formyl, C.sub.1-C.sub.3
alkylcarbonyl, C.sub.1-C.sub.3 haloalkylcarbonyl, cyano, or a group
of the formula
--CR.sup.17.dbd.CR.sup.18--SiR.sup.19R.sup.20R.sup.21, wherein
R.sup.17 is hydrogen, F, or Cl; R.sup.18 is hydrogen, F, Cl,
C.sub.1-C.sub.4 alkyl, or C.sub.1-C.sub.4 haloalkyl; and R.sup.19,
R.sup.20, and R.sup.21 are independently C.sub.1-C.sub.10 alkyl,
C.sub.3-C.sub.6 cycloalkyl, phenyl, substituted phenyl,
C.sub.1-C.sub.10 alkoxy, or OH; R.sup.3 and R.sup.4 are
independently hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6
haloalkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 haloalkenyl,
C.sub.3-C.sub.6 alkynyl, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl,
C.sub.1-C.sub.6 alkylcarbamyl, C.sub.1-C.sub.6 alkylsulfonyl,
C.sub.1-C.sub.6 trialkylsilyl, C.sub.1-C.sub.6 dialkylphosphonyl,
or R.sup.3 and R.sup.4 taken together with N is a 5- or 6-membered
saturated ring, or R.sup.3 and R.sup.4 taken together represent
.dbd.CR.sup.3'(R.sup.4'), wherein R.sup.3' and R.sup.4' are
independently hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.3-C.sub.6
alkenyl, C.sub.3-C.sub.6 alkynyl, C.sub.1-C.sub.6 alkoxy or
C.sub.1-C.sub.6 alkylamino, or, R.sup.3' and R.sup.4' taken
together with .dbd.C represent a 5- or 6-membered saturated ring; A
is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14,
A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27,
A28, A29, A30, A31, A32, A33, A34, A35, or A36; R.sup.5 is
hydrogen, halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
haloalkyl, cyclopropyl, halocyclopropyl, C.sub.2-C.sub.4 alkenyl,
C.sub.2-C.sub.4 haloalkenyl, C.sub.2-C.sub.4 alkynyl,
C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3
alkylthio, C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4
alkylamino, C.sub.2-C.sub.4 haloalkylamino, OH, or CN; R.sup.6,
R.sup.6', and R.sup.6'' are independently hydrogen, halogen,
C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, cyclopropyl,
halocyclopropyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4
haloalkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy,
C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio,
C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino or
C.sub.2-C.sub.4 haloalkylamino, OH, CN, or NO.sub.2; R.sup.7 and
R.sup.7' are independently hydrogen, halogen, C.sub.1-C.sub.4
alkyl, C.sub.1-C.sub.4 haloalkyl, cyclopropyl, halocyclopropyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3
haloalkoxy, C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, or phenyl; and R.sup.8 is hydrogen, C.sub.1-C.sub.6
alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6 alkenyl,
C.sub.3-C.sub.6 haloalkenyl, C.sub.3-C.sub.6 alkynyl, formyl,
C.sub.1-C.sub.3 alkylcarbonyl, C.sub.1-C.sub.3 haloalkylcarbonyl,
C.sub.1-C.sub.6 alkoxycarbonyl, C.sub.1-C.sub.6 alkylcarbamyl,
C.sub.1-C.sub.6 alkylsulfonyl, C.sub.1-C.sub.6 trialkylsilyl, or
phenyl; or an agriculturally acceptable N-oxide or salt
thereof.
18. The method of claim 16, wherein R.sup.1 is OR.sup.1', wherein
R.sup.1' is hydrogen, C.sub.1-C.sub.8 alkyl, or C.sub.7-C.sub.10
arylalkyl; R.sup.2 is halogen, C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4
haloalkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4 alkylthio, or
C.sub.1-C.sub.4 haloalkylthio; R.sup.3 and R.sup.4 are hydrogen,
C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6
alkenyl, C.sub.3-C.sub.6 haloalkenyl, C.sub.3-C.sub.6 alkynyl,
formyl, C.sub.1-C.sub.3 alkylcarbonyl, C.sub.1-C.sub.3
haloalkylcarbonyl, or R.sup.3 and R.sup.4 taken together represent
.dbd.CR.sup.3'(R.sup.4'), wherein R.sup.3' and R.sup.4' are
independently hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.3-C.sub.6
alkenyl, C.sub.3-C.sub.6 alkynyl, C.sub.1-C.sub.6 alkoxy or
C.sub.1-C.sub.6 alkylamino; A is A1, A2, A3, A7, A8, A9, A10, A11,
A12, A13, A14, A15, A21, A22, A23, A24, A27, A28, A29, A30, A31, or
A32; R.sup.5 is hydrogen, halogen, C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4
haloalkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy,
C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio,
C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino,
or C.sub.2-C.sub.4 haloalkylamino; R.sup.6, R.sup.6', and R.sup.6''
are independently hydrogen, halogen, C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, cyclopropyl, halocyclopropyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3
haloalkoxy, CN, or NO.sub.2; R.sup.7 and R.sup.7' are independently
hydrogen, halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
haloalkyl, C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3 haloalkoxy,
C.sub.1-C.sub.3 alkylthio, cyclopropyl, amino or C.sub.1-C.sub.4
alkylamino; and R.sup.8 is hydrogen, C.sub.1-C.sub.6 alkyl,
C.sub.1-C.sub.4 haloalkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6
haloalkenyl, formyl, C.sub.1-C.sub.3 alkylcarbonyl, C.sub.1-C.sub.3
haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl, or
C.sub.1-C.sub.6 alkylcarbamyl.
19. The method of claim 16, wherein the pyridine carboxylic acid
herbicide comprises a compound defined by Formula (III):
##STR00071## wherein X is N or CY, wherein Y is hydrogen, halogen,
C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 haloalkyl, C.sub.1-C.sub.3
alkoxy, C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio or
C.sub.1-C.sub.3 haloalkylthio; R.sup.1 is OR.sup.1' or
NR.sup.1''R.sup.1''', wherein R.sup.1' is hydrogen, C.sub.1-C.sub.8
alkyl, or C.sub.7-C.sub.10 arylalkyl, and R.sup.1'' and R.sup.1'''
are independently hydrogen, C.sub.1-C.sub.12 alkyl,
C.sub.3-C.sub.12 alkenyl, or C.sub.3-C.sub.12 alkynyl; R.sup.2 is
halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, cyano, or a group of the formula
--CR.sup.17.dbd.CR.sup.18--SiR.sup.19R.sup.20R.sup.21, wherein
R.sup.17 is hydrogen, F, or Cl; R.sup.18 is hydrogen, F, Cl,
C.sub.1-C.sub.4 alkyl, or C.sub.1-C.sub.4 haloalkyl; and R.sup.19,
R.sup.20, and R.sup.21 are independently C.sub.1-C.sub.10 alkyl,
C.sub.3-C.sub.6 cycloalkyl, phenyl, substituted phenyl,
C.sub.1-C.sub.10 alkoxy, or OH; R.sup.3 and R.sup.4 are
independently hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6
haloalkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 haloalkenyl,
C.sub.3-C.sub.6 alkynyl, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl,
C.sub.1-C.sub.6 alkylcarbamyl, C.sub.1-C.sub.6 alkylsulfonyl,
C.sub.1-C.sub.6 trialkylsilyl, C.sub.1-C.sub.6 dialkylphosphonyl,
or R.sup.3 and R.sup.4 taken together with N is a 5- or 6-membered
saturated ring, or R.sup.3 and R.sup.4 taken together represent
.dbd.CR.sup.3'(R.sup.4'), wherein R.sup.3' and R.sup.4' are
independently hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.3-C.sub.6
alkenyl, C.sub.3-C.sub.6 alkynyl, C.sub.1-C.sub.6 alkoxy or
C.sub.1-C.sub.6 alkylamino, or, R.sup.3' and R.sup.4' taken
together with .dbd.C represent a 5- or 6-membered saturated ring;
R.sup.6 and R.sup.6' are independently hydrogen, halogen,
C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, cyclopropyl,
halocyclopropyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4
haloalkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy,
C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio,
C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino or
C.sub.2-C.sub.4 haloalkylamino, OH, CN, or NO.sub.2; R.sup.7 and
R.sup.7' are independently hydrogen, halogen, C.sub.1-C.sub.4
alkyl, C.sub.1-C.sub.4 haloalkyl, cyclopropyl, halocyclopropyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3
haloalkoxy, C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, or phenyl; and R.sup.8 is hydrogen, C.sub.1-C.sub.6
alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6 alkenyl,
C.sub.3-C.sub.6 haloalkenyl, C.sub.3-C.sub.6 alkynyl, formyl,
C.sub.1-C.sub.3 alkylcarbonyl, C.sub.1-C.sub.3 haloalkylcarbonyl,
C.sub.1-C.sub.6 alkoxycarbonyl, C.sub.1-C.sub.6 alkylcarbamyl,
C.sub.1-C.sub.6 alkylsulfonyl, C.sub.1-C.sub.6 trialkylsilyl, or
phenyl; or an agriculturally acceptable N-oxide or salt
thereof.
20. The method of claim 1, wherein the pyridine carboxylic acid
herbicide comprises one of the following: ##STR00072##
##STR00073##
21. The method of claim 16, wherein the pyridine carboxylic acid
herbicide comprises ##STR00074##
22. The method of claim 16, wherein (b) is a
4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor
herbicide.
23. The method of claim 22, wherein the 4-hydroxyphenyl-pyruvate
dioxygenase (HPPD) inhibitor herbicide is selected from the group
consisting of benzobicyclon, benzofenap, bicyclopyrone,
fenquinotrione, isoxachlortole, isoxaflutole, mesotrione,
pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tembotrione,
tefuryltrione, topramezone, or an agriculturally acceptable salt
thereof, and combinations thereof.
24. The method of claim 23, wherein the weight ratio of (a) to (b)
is within the range from about 1:8000 to about 1000:1.
25. The method of claim 24, wherein the weight ratio of (a) to (b)
is within the range from about 1:500 to about 60:1.
26. The method of claim 25, wherein the weight ratio of (a) to (b)
is within the range from about 1:30 to about 5:1.
27. The method of claim 16, wherein (a) is applied in amount of
from 0.5 g ae/ha to 300 g ae/ha.
28. The method of claim 16, wherein (a) is applied in amount of
from 5 g ae/ha to 40 g ae/ha.
29. The method of claim 16, wherein (b) is applied in amount of
from 1 g ai/ha to 4500 g ai/ha.
30. The method of claim 16, wherein (b) is applied in amount of
from 1 g ai/ha to 1000 g ai/ha.
31. The method of claim 16, wherein (a) and (b) are applied
simultaneously.
32. The method of claim 16, wherein (a) and (b) are applied
post-emergence to the undesirable vegetation.
33. The method of claim 16, further comprising applying an
agriculturally acceptable adjuvant or carrier.
34. The method of claim 16, further comprising applying an
additional pesticide.
35. The method of claim 16, wherein the undesirable vegetation is
controlled in a glyphosate-, glufosinate-, dicamba-, phenoxy
auxin-, pyridyloxy auxin-, aryloxyphenoxypropionate-, acetyl CoA
carboxylase (ACCase) inhibitor-, imidazolinone-,
4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor-,
protoporphyrinogen oxidase (PPO) inhibitor-, triazine-, or
bromoxynil-tolerant crop.
36. The method of claim 35, wherein the tolerant crop possesses
multiple or stacked traits conferring tolerance to multiple
herbicides or multiple modes of action
37. The method of claim 16, wherein the undesirable vegetation
includes a broadleaf weed and/or a grass weed.
38. The method of claim 16, wherein the undesirable vegetation
comprises a herbicide resistant or tolerant weed.
39. The method of claim 38, wherein the resistant or tolerant weed
is a biotype with resistance or tolerance to multiple herbicides,
multiple chemical classes, or multiple herbicide
modes-of-action.
40. The method of claim 38, wherein the resistant or tolerant weed
is a biotype resistant or tolerant to photosystem II inhibitors,
acetyl CoA carboxylase (ACCase) inhibitors, synthetic auxins,
photosystem I inhibitors, 5-enolpyruvylshikimate-3-phosphate (EPSP)
synthase inhibitors, microtubule assembly inhibitors, lipid
synthesis inhibitors, protoporphyrinogen oxidase (PPO) inhibitors,
carotenoid biosynthesis inhibitors, very long chain fatty acid
(VLCFA) inhibitors, phytoene desaturase (PDS) inhibitors, glutamine
synthetase inhibitors, 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD)
inhibitors, mitosis inhibitors, cellulose biosynthesis inhibitors,
herbicides with multiple modes-of-action, quinclorac,
arylaminopropionic acids, difenzoquat, endothall, or
organoarsenicals.
41. The method of claim 16, wherein the undesirable vegetation
includes velvetleaf, pigweed, wild oat, winter rape, lambsquarters,
thistle, barnyardgrass, poinsettia, soybean, sunflower, ivyleaf
morningglory, kochia, wild buckwheat, giant foxtail, sorghum,
common chickweed, wild pansy, or a combination thereof.
42. The method of claim 16, wherein the active ingredients applied
to the vegetation or an area adjacent the vegetation or applied to
soil or water to control the emergence or growth of vegetation
consist of (a) and (b).
43. The composition of claim 8, wherein the wherein the
4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor herbicide is
pyransulfotole.
44. The composition of claim 8, wherein the wherein the
4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor herbicide is
pyrazolynate.
45. The composition of claim 8, wherein the wherein the
4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor herbicide is
sulcotrione.
46. The composition of claim 8, wherein the wherein the
4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor herbicide is
tembotrione.
47. The composition of claim 8, wherein the wherein the
4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor herbicide is
isoxaflutole.
48. The composition of claim 8, wherein the wherein the
4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor herbicide is
mesotrione.
49. The composition of claim 43, further comprising bromoxynil,
wherein the ratio of bromoxynil to pyransulfotole is between about
10:1 to about 1:10.
50. The composition of claim 49, wherein the ratio of bromoxynil to
pyransulfotole is between about 7:1 to about 1:1.
51. The composition of claim 50, wherein the ratio of bromoxynil to
pyransulfotole is between about 6:1 to about 5:1.
Description
CROSS-REFERENCE TO RELATED APPLICATIONS
[0001] This application claims priority to U.S. Provisional
Application Ser. No. 62/652,377, filed on Apr. 4, 2018, the entire
disclosure of which is hereby expressly incorporated by
reference.
BACKGROUND
[0002] Many recurring problems in agriculture involve controlling
growth of undesirable vegetation that can, for instance, inhibit
crop growth. To help control undesirable vegetation, researchers
have produced a variety of chemicals and chemical formulations
effective in controlling such unwanted growth. However, a
continuing need exists for new compositions and methods to control
growth of undesirable vegetation.
SUMMARY OF THE DISCLOSURE
[0003] Disclosed herein are herbicidal compositions containing a
herbicidally effective amount of (a) a pyridine carboxylic acid
herbicide or an agriculturally acceptable N-oxide, salt, or ester
thereof, and (b) a 4-hydroxyphenyl-pyruvate dioxygenase (HPPD)
inhibitor or an agriculturally acceptable salt or ester thereof. In
some embodiments, the weight ratio of (a) to (b) can be from 1:8000
to 1000:1 (e.g., from 1:2000 to 250:1, from 1:500 to 60:1, from
1:125 to 15:1, or from 1:30 to 5:1).
[0004] The pyridine carboxylic acid herbicide can comprise a
compound defined by Formula (I)
##STR00001##
wherein
[0005] X is N or CY, wherein Y is hydrogen, halogen,
C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 haloalkyl, C.sub.1-C.sub.3
alkoxy, C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio or
C.sub.1-C.sub.3 haloalkylthio;
[0006] R.sup.1 is OR.sup.1' or NR.sup.1''R.sup.1''', wherein
R.sup.1' is hydrogen, C.sub.1-C.sub.8 alkyl, or C.sub.7-C.sub.10
arylalkyl, and R.sup.1'' and R.sup.1''' are independently hydrogen,
C.sub.1-C.sub.12 alkyl, C.sub.3-C.sub.12 alkenyl, or
C.sub.3-C.sub.12 alkynyl;
[0007] R.sup.2 is halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
haloalkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, cyano, or a group of the formula
--CR.sup.17.dbd.CR.sup.18--SiR.sup.19R.sup.20R.sup.21, wherein
R.sup.17 is hydrogen, F, or Cl; R.sup.18 is hydrogen, F, Cl,
C.sub.1-C.sub.4 alkyl, or C.sub.1-C.sub.4 haloalkyl; and R.sup.19,
R.sup.20, and R.sup.21 are independently C.sub.1-C.sub.10 alkyl,
C.sub.3-C.sub.6 cycloalkyl, phenyl, substituted phenyl,
C.sub.1-C.sub.10 alkoxy, or OH;
[0008] R.sup.3 and R.sup.4 are independently hydrogen,
C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6
alkenyl, C.sub.3-C.sub.6 haloalkenyl, C.sub.3-C.sub.6 alkynyl,
formyl, C.sub.1-C.sub.3 alkylcarbonyl, C.sub.1-C.sub.3
haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl, C.sub.1-C.sub.6
alkylcarbamyl, C.sub.1-C.sub.6 alkylsulfonyl, C.sub.1-C.sub.6
trialkylsilyl, C.sub.1-C.sub.6 dialkylphosphonyl, or R.sup.3 and
R.sup.4 taken together with N is a 5- or 6-membered saturated ring,
or R.sup.3 and R.sup.4 taken together represent
.dbd.CR.sup.3'(R.sup.4'), wherein R.sup.3' and R.sup.4' are
independently hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.3-C.sub.6
alkenyl, C.sub.3-C.sub.6 alkynyl, C.sub.1-C.sub.6 alkoxy or
C.sub.1-C.sub.6 alkylamino, or, R.sup.3' and R.sup.4' taken
together with .dbd.C represent a 5- or 6-membered saturated
ring;
[0009] A is one of groups A1 to A36
##STR00002## ##STR00003## ##STR00004## ##STR00005## ##STR00006##
##STR00007##
[0010] R.sup.5, if applicable to the A group, is hydrogen, halogen,
C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, cyclopropyl,
halocyclopropyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4
haloalkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy,
C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio,
C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino,
C.sub.2-C.sub.4 haloalkylamino, OH, or CN;
[0011] R.sup.6, R.sup.6', and R.sup.6'', if applicable to the A
group, are independently hydrogen, halogen, C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, cyclopropyl, halocyclopropyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3
haloalkoxy, C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino or C.sub.2-C.sub.4
haloalkylamino, OH, CN, or NO.sub.2;
[0012] R.sup.7 and R.sup.7' are independently hydrogen, halogen,
C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, cyclopropyl,
halocyclopropyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4
haloalkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy,
C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio,
C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino,
C.sub.1-C.sub.4 haloalkylamino, or phenyl;
[0013] R.sup.8 is hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6
haloalkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 haloalkenyl,
C.sub.3-C.sub.6 alkynyl, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl,
C.sub.1-C.sub.6 alkylcarbamyl, C.sub.1-C.sub.6 alkylsulfonyl,
C.sub.1-C.sub.6 trialkylsilyl, or phenyl;
[0014] or an agriculturally acceptable N-oxide or salt thereof.
[0015] In certain embodiments, the pyridine carboxylic acid
herbicide can comprise a compound defined by Formula (II):
##STR00008##
wherein
[0016] R.sup.1 is OR.sup.1' or NR.sup.1''R.sup.1''', wherein
R.sup.1' is hydrogen, C.sub.1-C.sub.8 alkyl, or C.sub.7-C.sub.10
arylalkyl, and R.sup.1'' and R.sup.1''' are independently hydrogen,
C.sub.1-C.sub.12 alkyl, C.sub.3-C.sub.12 alkenyl, or
C.sub.3-C.sub.12 alkynyl;
[0017] R.sup.2 is halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
haloalkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, cyano, or a group of the formula
--CR.sup.17.dbd.CR.sup.18--SiR.sup.19R.sup.20R.sup.21, wherein
R.sup.17 is hydrogen, F, or Cl; R.sup.18 is hydrogen, F, Cl,
C.sub.1-C.sub.4 alkyl, or C.sub.1-C.sub.4 haloalkyl; and R.sup.19,
R.sup.20, and R.sup.21 are independently C.sub.1-C.sub.10 alkyl,
C.sub.3-C.sub.6 cycloalkyl, phenyl, substituted phenyl,
C.sub.1-C.sub.10 alkoxy, or OH;
[0018] R.sup.3 and R.sup.4 are independently hydrogen,
C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6
alkenyl, C.sub.3-C.sub.6 haloalkenyl, C.sub.3-C.sub.6 alkynyl,
formyl, C.sub.1-C.sub.3 alkylcarbonyl, C.sub.1-C.sub.3
haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl, C.sub.1-C.sub.6
alkylcarbamyl, C.sub.1-C.sub.6 alkylsulfonyl, C.sub.1-C.sub.6
trialkylsilyl, C.sub.1-C.sub.6 dialkylphosphonyl, or R.sup.3 and
R.sup.4 taken together with N is a 5- or 6-membered saturated ring,
or R.sup.3 and R.sup.4 taken together represent
.dbd.CR.sup.3'(R.sup.4'), wherein R.sup.3' and R.sup.4' are
independently hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.3-C.sub.6
alkenyl, C.sub.3-C.sub.6 alkynyl, C.sub.1-C.sub.6 alkoxy or
C.sub.1-C.sub.6 alkylamino, or, R.sup.3' and R.sup.4' taken
together with .dbd.C represent a 5- or 6-membered saturated
ring;
[0019] A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13,
A14, A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26,
A27, A28, A29, A30, A31, A32, A33, A34, A35, or A36;
[0020] R.sup.5 is hydrogen, halogen, C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, cyclopropyl, halocyclopropyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3
haloalkoxy, C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, OH, or CN;
[0021] R.sup.6, R.sup.6', and R.sup.6'' are independently hydrogen,
halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl,
cyclopropyl, halocyclopropyl, C.sub.2-C.sub.4 alkenyl,
C.sub.2-C.sub.4 haloalkenyl, C.sub.2-C.sub.4 alkynyl,
C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3
alkylthio, C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4
alkylamino or C.sub.2-C.sub.4 haloalkylamino, OH, CN, or
NO.sub.2;
[0022] R.sup.7 and R.sup.7' are independently hydrogen, halogen,
C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, cyclopropyl,
halocyclopropyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4
haloalkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy,
C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio,
C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino,
C.sub.2-C.sub.4 haloalkylamino, or phenyl; and
[0023] R.sup.8 is hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6
haloalkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 haloalkenyl,
C.sub.3-C.sub.6 alkynyl, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl,
C.sub.1-C.sub.6 alkylcarbamyl, C.sub.1-C.sub.6 alkylsulfonyl,
C.sub.1-C.sub.6 trialkylsilyl, or phenyl;
[0024] or an agriculturally acceptable N-oxide or salt thereof.
[0025] In some embodiments, R.sup.1 is OR.sup.1', wherein R.sup.1'
is hydrogen, C.sub.1-C.sub.8 alkyl, or C.sub.7-C.sub.10 arylalkyl.
In certain embodiments, R.sup.2 is Cl, methoxy, vinyl, or
1-propenyl; R.sup.3 and R.sup.4 are hydrogen; A is A15; R.sup.5 is
hydrogen or F; and R.sup.6 is hydrogen or F; and R.sup.6'' is
hydrogen, halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
haloalkyl, cyclopropyl, C.sub.2-C.sub.4 alkynyl, CN, or
NO.sub.2.
[0026] In certain embodiments, the pyridine carboxylic acid
herbicide can comprise a compound defined by Formula (III):
##STR00009##
wherein
[0027] X is N or CY, wherein Y is hydrogen, halogen,
C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 haloalkyl, C.sub.1-C.sub.3
alkoxy, C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio or
C.sub.1-C.sub.3 haloalkylthio;
[0028] R.sup.1 is OR.sup.1' or NR.sup.1''R.sup.1''', wherein
R.sup.1' is hydrogen, C.sub.1-C.sub.8 alkyl, or C.sub.7-C.sub.10
arylalkyl, and R.sup.1'' and R.sup.1''' are independently hydrogen,
C.sub.1-C.sub.12 alkyl, C.sub.3-C.sub.12 alkenyl, or
C.sub.3-C.sub.12 alkynyl;
[0029] R.sup.2 is halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
haloalkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, cyano, or a group of the formula
--CR.sup.17.dbd.CR.sup.18--SiR.sup.19R.sup.20R.sup.21, wherein
R.sup.17 is hydrogen, F, or Cl; R.sup.18 is hydrogen, F, Cl,
C.sub.1-C.sub.4 alkyl, or C.sub.1-C.sub.4 haloalkyl; and R.sup.19,
R.sup.20, and R.sup.21 are independently C.sub.1-C.sub.10 alkyl,
C.sub.3-C.sub.6 cycloalkyl, phenyl, substituted phenyl,
C.sub.1-C.sub.10 alkoxy, or OH;
[0030] R.sup.3 and R.sup.4 are independently hydrogen,
C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6
alkenyl, C.sub.3-C.sub.6 haloalkenyl, C.sub.3-C.sub.6 alkynyl,
formyl, C.sub.1-C.sub.3 alkylcarbonyl, C.sub.1-C.sub.3
haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl, C.sub.1-C.sub.6
alkylcarbamyl, C.sub.1-C.sub.6 alkylsulfonyl, C.sub.1-C.sub.6
trialkylsilyl, C.sub.1-C.sub.6 dialkylphosphonyl, or R.sup.3 and
R.sup.4 taken together with N is a 5- or 6-membered saturated ring,
or R.sup.3 and R.sup.4 taken together represent
.dbd.CR.sup.3'(R.sup.4'), wherein R.sup.3' and R.sup.4' are
independently hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.3-C.sub.6
alkenyl, C.sub.3-C.sub.6 alkynyl, C.sub.1-C.sub.6 alkoxy or
C.sub.1-C.sub.6 alkylamino, or, R.sup.3' and R.sup.4' taken
together with .dbd.C represent a 5- or 6-membered saturated
ring;
[0031] R.sup.6 and R.sup.6' are independently hydrogen, halogen,
C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, cyclopropyl,
halocyclopropyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4
haloalkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy,
C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio,
C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino or
C.sub.2-C.sub.4 haloalkylamino, OH, CN, or NO.sub.2;
[0032] R.sup.7 and R.sup.7' are independently hydrogen, halogen,
C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, cyclopropyl,
halocyclopropyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4
haloalkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy,
C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio,
C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino,
C.sub.2-C.sub.4 haloalkylamino, or phenyl; and
[0033] R.sup.8 is hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6
haloalkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 haloalkenyl,
C.sub.3-C.sub.6 alkynyl, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl,
C.sub.1-C.sub.6 alkylcarbamyl, C.sub.1-C.sub.6 alkylsulfonyl,
C.sub.1-C.sub.6 trialkylsilyl, or phenyl;
[0034] or an agriculturally acceptable N-oxide or salt thereof.
[0035] In some embodiments, X is N, CH or CF. In certain
embodiments, X is CF, R.sup.1 is OR.sup.1', wherein R.sup.1' is
hydrogen, C.sub.1-C.sub.8 alkyl, or C.sub.7-C.sub.10 arylalkyl;
R.sup.2 is Cl, methoxy, vinyl, or 1-propenyl; R.sup.3 and R.sup.4
are hydrogen; R.sup.6 is hydrogen or F; and R.sup.6' is hydrogen,
halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl,
cyclopropyl, C.sub.2-C.sub.4 alkynyl, CN, or NO.sub.2.
[0036] In certain embodiments, the pyridine carboxylic acid
herbicide can include
4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl) picolinic acid
or an agriculturally acceptable N-oxide, salt, or ester
thereof.
[0037] In some embodiments, (b) can comprise an HPPD inhibitor. In
certain embodiments, (b) can include benzobicyclon, benzofenap,
bicyclopyrone, fenquinotrione, isoxachlortole, isoxaflutole,
mesotrione, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione,
tembotrione, tefuryltrione, topramezone, or an agriculturally
acceptable salt thereof of at least one of the aforementioned HPPD
inhibitors, or combinations thereof.
[0038] The composition can further comprise an additional
pesticide, a herbicidal safener, an agriculturally acceptable
adjuvant or carrier, or a combination thereof. The composition can
be provided as a herbicidal concentrate.
[0039] The present disclosure also relates to methods of
controlling undesirable vegetation which comprise applying to
vegetation or an area adjacent the vegetation or applying to soil
or water to prevent the emergence or growth of vegetation a
herbicidally effective amount of (a) a pyridine carboxylic acid
herbicide or an agriculturally acceptable N-oxide, salt, or ester
thereof and (b) a 4-hydroxyphenyl-pyruvate dioxygenase (HPPD)
inhibitor or an agriculturally acceptable salt thereof. In some
embodiments, (a) and (b) are applied simultaneously. In some
embodiments, (a) and (b) are applied post-emergence to the
undesirable vegetation.
[0040] In some embodiments, (a) can comprise a pyridine carboxylic
acid herbicide described above. In certain embodiments, (a) can
comprise 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)
picolinic acid or an agriculturally acceptable N-oxide, salt, or
ester thereof. In some embodiments, (b) can comprise a
4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor. In certain
embodiments, (b) can include benzobicyclon, benzofenap,
bicyclopyrone, fenquinotrione, isoxachlortole, isoxaflutole,
mesotrione, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione,
tembotrione, tefuryltrione, topramezone, or an agriculturally
acceptable salt thereof. In some cases, (a) can be applied in an
amount of from 0.5 grams acid equivalent per hectare (g ae/ha) to
300 g ae/ha (e.g., from 5 g ae/ha to 40 g ae/ha) and (b) can be
applied in an amount of from 1 gram active ingredient per hectare
(g ai/ha) to 4000 g ai/ha (e.g., from 1 g ai/ha to 1000 g ai/ha).
In some cases, (a) and (b) can be applied in a weight ratio of from
1:8000 to 1000:1 (e.g., from 1:2000 to 250:1, from 1:500 to 60:1,
from 1:125 to 15:1, or from 1:30 to 5:1).
[0041] The description below sets forth details of one or more
embodiments of the present disclosure. Other features, objects, and
advantages will be apparent from the description and from the
claims.
DETAILED DESCRIPTION
[0042] The present disclosure relates to herbicidal compositions
containing a herbicidally effective amount of (a) a pyridine
carboxylic acid herbicide or an agriculturally acceptable N-oxide,
salt, or ester thereof and (b) a 4-hydroxyphenyl-pyruvate
dioxygenase (HPPD) inhibitor or an agriculturally acceptable salt
thereof. The present disclosure also relates to methods for
controlling undesirable vegetation.
I. Definitions
[0043] Terms used herein will have their customary meaning in the
art unless specified otherwise. The organic moieties mentioned when
defining variable positions within the general formulae described
herein (e.g., the term "halogen") are collective terms for the
individual substituents encompassed by the organic moiety. The
prefix C.sub.n-C.sub.m preceding a group or moiety indicates, in
each case, the possible number of carbon atoms in the group or
moiety that follows.
[0044] As used herein, the terms "herbicide" and "herbicidal active
ingredient" refer to an active ingredient that kills, controls, or
otherwise adversely modifies the growth of vegetation, particularly
undesirable vegetation, such as weeds, when applied in an
appropriate amount.
[0045] As used herein, a "herbicidally effective amount" refers to
an amount of an active ingredient that causes a "herbicidal
effect," such as an adversely modifying effect including, for
instance, a deviation from natural growth or development, killing,
regulation, desiccation, growth inhibition, growth reduction, and
retardation.
[0046] As used herein, applying a herbicide or herbicidal
composition refers to delivering it directly to the targeted
vegetation or to the locus thereof or to the area where control of
undesired vegetation is desired. Methods of application include,
but are not limited to pre-emergently contacting soil or water,
post-emergently contacting the undesirable vegetation or area
adjacent to the undesirable vegetation.
[0047] As used herein, the terms "crops" and "vegetation" can
include, for instance, dormant seeds, germinant seeds, emerging
seedlings, plants emerging from vegetative propagules, immature
vegetation, and established vegetation.
[0048] As used herein, immature vegetation refers to small
vegetative plants prior to reproductive stage, and mature
vegetation refers to vegetative plants during and after the
reproductive stage.
[0049] As used herein, unless otherwise specified, the term "acyl"
refers to a group of formula --C(O)R, where R is hydrogen, alkyl
(e.g., C.sub.1-C.sub.10 alkyl), haloalkyl (C.sub.1-C.sub.8
haloalkyl), alkenyl (C.sub.2-C.sub.8 alkenyl), haloalkenyl (e.g.,
C.sub.2-C.sub.8 haloalkenyl), alkynyl (e.g., C.sub.2-C.sub.8
alkynyl), alkoxy (C.sub.1-C.sub.8 alkoxy), haloalkoxy
(C.sub.1-C.sub.8 alkoxy), aryl, or heteroaryl, arylalkyl
(C.sub.7-C.sub.10 arylalkyl), as defined below, where "C(O)" or
"CO" is short-hand notation for C.dbd.O. In some embodiments, the
acyl group can be a C.sub.1-C.sub.6 acyl group (e.g., a formyl
group, a C.sub.1-C.sub.5 alkylcarbonyl group, or a C.sub.1-C.sub.5
haloalkylcarbonyl group). In some embodiments, the acyl group can
be a C.sub.1-C.sub.3 acyl group (e.g., a formyl group, a
C.sub.1-C.sub.3 alkylcarbonyl group, or a C.sub.1-C.sub.3
haloalkylcarbonyl group).
[0050] As used herein, the term "alkyl" refers to saturated,
straight-chained or branched saturated hydrocarbon moieties. Unless
otherwise specified, C.sub.1-C.sub.20 (e.g., C.sub.1-C.sub.12,
C.sub.1-C.sub.10, C.sub.1-C.sub.8, C.sub.1-C.sub.6,
C.sub.1-C.sub.4) alkyl groups are intended. Examples of alkyl
groups include methyl, ethyl, propyl, 1-methyl-ethyl, butyl,
1-methyl-propyl, 2-methyl-propyl, 1,1-dimethyl-ethyl, pentyl,
1-methyl-butyl, 2-methyl-butyl, 3-methyl-butyl,
2,2-dimethyl-propyl, 1-ethyl-propyl, hexyl, 1,1-dimethyl-propyl,
1,2-dimethyl-propyl, 1-methyl-pentyl, 2-methyl-pentyl,
3-methyl-pentyl, 4-methyl-pentyl, 1,1-dimethyl-butyl,
1,2-dimethyl-butyl, 1,3-dimethyl-butyl, 2,2-dimethyl-butyl,
2,3-dimethyl-butyl, 3,3-dimethyl-butyl, 1-ethyl-butyl,
2-ethyl-butyl, 1,1,2-trimethyl-propyl, 1,2,2-trimethyl-propyl,
1-ethyl-1-methyl-propyl, and 1-ethyl-2-methyl-propyl. Alkyl
substituents may be unsubstituted or substituted with one or more
chemical moieties. Examples of suitable substituents include, for
example, hydroxy, nitro, cyano, formyl, C.sub.1-C.sub.6 alkoxy,
C.sub.1-C.sub.6 haloalkoxy, C.sub.1-C.sub.6 acyl, C.sub.1-C.sub.6
alkylthio, C.sub.1-C.sub.6 haloalkylthio, C.sub.1-C.sub.6
alkylsulfinyl, C.sub.1-C.sub.6 haloalkylsulfinyl, C.sub.1-C.sub.6
alkylsulfonyl, C.sub.1-C.sub.6 haloalkylsulfonyl, C.sub.1-C.sub.6
alkoxycarbonyl, C.sub.1-C.sub.6 haloalkoxycarbonyl, C.sub.1-C.sub.6
carbamoyl, C.sub.1-C.sub.6 halocarbamoyl, hydroxycarbonyl,
C.sub.1-C.sub.6 alkylcarbonyl, C.sub.1-C.sub.6 haloalkylcarbonyl,
aminocarbonyl, C.sub.1-C.sub.6 alkylaminocarbonyl,
haloalkylaminocarbonyl, C.sub.1-C.sub.6 dialkylaminocarbonyl, and
C.sub.1-C.sub.6 dihaloalkylaminocarbonyl, provided that the
substituents are sterically compatible and the rules of chemical
bonding and strain energy are satisfied. Preferred substituents
include cyano and C.sub.1-C.sub.6 alkoxy.
[0051] As used herein, the term "haloalkyl" refers to
straight-chained or branched alkyl groups, wherein these groups the
hydrogen atoms may partially or entirely be substituted with
halogen atoms. Unless otherwise specified, C.sub.1-C.sub.20 (e.g.,
C.sub.1-C.sub.12, C.sub.1-C.sub.10, C.sub.1-C.sub.8,
C.sub.1-C.sub.6, C.sub.1-C.sub.4) alkyl groups are intended.
Examples include chloromethyl, bromomethyl, dichloromethyl,
trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl,
chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl,
1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl,
2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,
2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,
2,2,2-trichloroethyl, pentafluoroethyl, and
1,1,1-trifluoroprop-2-yl. Haloalkyl substituents may be
unsubstituted or substituted with one or more chemical moieties.
Examples of suitable substituents include, for example, hydroxy,
nitro, cyano, formyl, C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6
haloalkoxy, C.sub.1-C.sub.6 acyl, C.sub.1-C.sub.6 alkylthio,
C.sub.1-C.sub.6 haloalkylthio, C.sub.1-C.sub.6 alkylsulfinyl,
C.sub.1-C.sub.6 haloalkylsulfinyl, C.sub.1-C.sub.6 alkylsulfonyl,
C.sub.1-C.sub.6 haloalkylsulfonyl, C.sub.1-C.sub.6 alkoxycarbonyl,
C.sub.1-C.sub.6 haloalkoxycarbonyl, C.sub.1-C.sub.6 carbamoyl,
C.sub.1-C.sub.6 halocarbamoyl, hydroxycarbonyl, C.sub.1-C.sub.6
alkylcarbonyl, C.sub.1-C.sub.6 haloalkylcarbonyl, aminocarbonyl,
C.sub.1-C.sub.6 alkylaminocarbonyl, haloalkylaminocarbonyl,
C.sub.1-C.sub.6 dialkylaminocarbonyl, and C.sub.1-C.sub.6
dihaloalkylaminocarbonyl, provided that the substituents are
sterically compatible and the rules of chemical bonding and strain
energy are satisfied. Preferred substituents include cyano and
C.sub.1-C.sub.6 alkoxy.
[0052] As used herein, the term "alkenyl" refers to unsaturated,
straight-chained, or branched hydrocarbon moieties containing a
double bond. Unless otherwise specified, C.sub.2-C.sub.20 (e.g.,
C.sub.2-C.sub.12, C.sub.2-C.sub.10, C.sub.2-C.sub.8,
C.sub.2-C.sub.6, C.sub.2-C.sub.4) alkenyl groups are intended.
Alkenyl groups may contain more than one unsaturated bond. Examples
include ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl,
1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl,
2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl,
1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl,
2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl,
2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl,
2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl,
1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl,
1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl,
3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl,
2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl,
1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl,
4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl,
3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl,
2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl,
1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl,
1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl,
1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl,
1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl,
2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl,
2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl,
3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl,
1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl,
2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl,
1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl, and
1-ethyl-2-methyl-2-propenyl. The term "vinyl" refers to a group
having the structure --CH.dbd.CH.sub.2; 1-propenyl refers to a
group with the structure --CH.dbd.CH--CH.sub.3; and 2-propenyl
refers to a group with the structure --CH.sub.2--CH.dbd.CH.sub.2.
Alkenyl substituents may be unsubstituted or substituted with one
or more chemical moieties. Examples of suitable substituents
include, for example, hydroxy, nitro, cyano, formyl,
C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6 haloalkoxy, C.sub.1-C.sub.6
acyl, C.sub.1-C.sub.6 alkylthio, C.sub.1-C.sub.6 haloalkylthio,
C.sub.1-C.sub.6 alkylsulfinyl, C.sub.1-C.sub.6 haloalkylsulfinyl,
C.sub.1-C.sub.6 alkylsulfonyl, C.sub.1-C.sub.6 haloalkylsulfonyl,
C.sub.1-C.sub.6 alkoxycarbonyl, C.sub.1-C.sub.6 haloalkoxycarbonyl,
C.sub.1-C.sub.6 carbamoyl, C.sub.1-C.sub.6 halocarbamoyl,
hydroxycarbonyl, C.sub.1-C.sub.6 alkylcarbonyl, C.sub.1-C.sub.6
haloalkylcarbonyl, aminocarbonyl, C.sub.1-C.sub.6
alkylaminocarbonyl, haloalkylaminocarbonyl, C.sub.1-C.sub.6
dialkylaminocarbonyl, and C.sub.1-C.sub.6 dihaloalkylaminocarbonyl,
provided that the substituents are sterically compatible and the
rules of chemical bonding and strain energy are satisfied.
Preferred substituents include cyano and C.sub.1-C.sub.6
alkoxy.
[0053] The term "haloalkenyl," as used herein, refers to an alkenyl
group, as defined above, which is substituted by one or more
halogen atoms.
[0054] As used herein, the term "alkynyl" represents
straight-chained or branched hydrocarbon moieties containing a
triple bond. Unless otherwise specified, C.sub.2-C.sub.20 (e.g.,
C.sub.2-C.sub.12, C.sub.2-C.sub.10, C.sub.2-C.sub.8,
C.sub.2-C.sub.6, C.sub.2-C.sub.4) alkynyl groups are intended.
Alkynyl groups may contain more than one unsaturated bond. Examples
include C.sub.2-C.sub.6-alkynyl, such as ethynyl, 1-propynyl,
2-propynyl (or propargyl), 1-butynyl, 2-butynyl, 3-butynyl,
1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl,
4-pentynyl, 3-methyl-1-butynyl, 1-methyl-2-butynyl,
1-methyl-3-butynyl, 2-methyl-3-butynyl, 1,1-dimethyl-2-propynyl,
1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl,
5-hexynyl, 3-methyl-1-pentynyl, 4-methyl-1-pentynyl,
1-methyl-2-pentynyl, 4-methyl-2-pentynyl, 1-methyl-3-pentynyl,
2-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-4-pentynyl,
3-methyl-4-pentynyl, 1,1-dimethyl-2-butynyl,
1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl,
2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl,
1-ethyl-3-butynyl, 2-ethyl-3-butynyl, and
1-ethyl-1-methyl-2-propynyl. Alkynyl substituents may be
unsubstituted or substituted with one or more chemical moieties.
Examples of suitable substituents include, for example, hydroxy,
nitro, cyano, formyl, C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6
haloalkoxy, C.sub.1-C.sub.6 acyl, C.sub.1-C.sub.6 alkylthio,
C.sub.1-C.sub.6 haloalkylthio, C.sub.1-C.sub.6 alkylsulfinyl,
C.sub.1-C.sub.6 haloalkylsulfinyl, C.sub.1-C.sub.6 alkylsulfonyl,
C.sub.1-C.sub.6 haloalkylsulfonyl, C.sub.1-C.sub.6 alkoxycarbonyl,
C.sub.1-C.sub.6 haloalkoxycarbonyl, C.sub.1-C.sub.6 carbamoyl,
C.sub.1-C.sub.6 halocarbamoyl, hydroxycarbonyl, C.sub.1-C.sub.6
alkylcarbonyl, C.sub.1-C.sub.6 haloalkylcarbonyl, aminocarbonyl,
C.sub.1-C.sub.6 alkylaminocarbonyl, haloalkylaminocarbonyl,
C.sub.1-C.sub.6 dialkylaminocarbonyl, and C.sub.1-C.sub.6
dihaloalkylaminocarbonyl, provided that the substituents are
sterically compatible and the rules of chemical bonding and strain
energy are satisfied. Preferred substituents include cyano and
C.sub.1-C.sub.6 alkoxy.
[0055] As used herein, the term "alkoxy" refers to a group of the
formula R--O--, where R is unsubstituted or substituted alkyl as
defined above. Unless otherwise specified, alkoxy groups wherein R
is a C.sub.1-C.sub.20 (e.g., C.sub.1-C.sub.12, C.sub.1-C.sub.10,
C.sub.1-C.sub.8, C.sub.1-C.sub.6, C.sub.1-C.sub.4) alkyl group are
intended. Examples include methoxy, ethoxy, propoxy,
1-methyl-ethoxy, butoxy, 1-methyl-propoxy, 2-methyl-propoxy,
1,1-dimethyl-ethoxy, pentoxy, 1-methyl-butyloxy, 2-methyl-butoxy,
3-methyl-butoxy, 2,2-di-methyl-propoxy, 1-ethyl-propoxy, hexoxy,
1,1-dimethyl-propoxy, 1,2-dimethyl-propoxy, 1-methyl-pentoxy,
2-methyl-pentoxy, 3-methyl-pentoxy, 4-methyl-penoxy,
1,1-dimethyl-butoxy, 1,2-dimethyl-butoxy, 1,3-dimethyl-butoxy,
2,2-dimethyl-butoxy, 2,3-dimethyl-butoxy, 3,3-dimethyl-butoxy,
1-ethyl-butoxy, 2-ethylbutoxy, 1,1,2-trimethyl-propoxy,
1,2,2-trimethyl-propoxy, 1-ethyl-1-methyl-propoxy, and
1-ethyl-2-methyl-propoxy.
[0056] As used herein, the term "haloalkoxy" refers to a group of
the formula R--O--, where R is unsubstituted or substituted
haloalkyl as defined above. Unless otherwise specified, haloalkoxy
groups wherein R is a C.sub.1-C.sub.20 (e.g., C.sub.1-C.sub.12,
C.sub.1-C.sub.10, C.sub.1-C.sub.8, C.sub.1-C.sub.6,
C.sub.1-C.sub.4) alkyl group are intended. Examples include
chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy,
fluoromethoxy, difluoromethoxy, trifluoromethoxy,
chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy,
1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy,
2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,
2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,
2,2,2-trichloroethoxy, pentafluoroethoxy, and
1,1,1-trifluoroprop-2-oxy.
[0057] As used herein, the term "alkylthio" refers to a group of
the formula R--S--, where R is unsubstituted or substituted alkyl
as defined above. Unless otherwise specified, alkylthio groups
wherein R is a C.sub.1-C.sub.20 (e.g., C.sub.1-C.sub.12,
C.sub.1-C.sub.4) alkyl group are intended. Examples include
methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio,
1-methyl-propylthio, 2-methylpropylthio, 1,1-dimethylethylthio,
pentylthio, 1-methylbutylthio, 2-methylbutylthio,
3-methylbutylthio, 2,2-di-methylpropylthio, 1-ethylpropylthio,
hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio,
1-methylpentylthio, 2-methylpentylthio, 3-methyl-pentylthio,
4-methyl-pentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio,
1,3-dimethylbutylthio, 2,2-dimethylbutylthio,
2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio,
2-ethylbutylthio, 1,1,2-trimethylpropylthio,
1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio, and
1-ethyl-2-methylpropylthio.
[0058] As used herein, the term "haloalkylthio" refers to an
alkylthio group as defined above wherein the carbon atoms are
partially or entirely substituted with halogen atoms. Unless
otherwise specified, haloalkylthio groups wherein R is a
C.sub.1-C.sub.20 (e.g., C.sub.1-C.sub.12, C.sub.1-C.sub.10,
C.sub.1-C.sub.8, C.sub.1-C.sub.6, C.sub.1-C.sub.4) alkyl group are
intended. Examples include chloromethylthio, bromomethylthio,
dichloromethylthio, trichloromethylthio, fluoromethylthio,
difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio,
dichlorofluoro-methylthio, chlorodifluoromethylthio,
1-chloroethylthio, 1-bromoethylthio, 1-fluoroethylthio,
2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio,
2-chloro-2-fluoroethylthio, 2-chloro-2-difluoroethylthio,
2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio,
pentafluoroethylthio, and 1,1,1-trifluoroprop-2-ylthio.
[0059] As used herein, the term "aryl," as well as derivative terms
such as aryloxy, refers to groups that include a monovalent
aromatic carbocyclic group of from 6 to 14 carbon atoms. Aryl
groups can include a single ring or multiple condensed rings. In
some embodiments, aryl groups include C.sub.6-C.sub.10 aryl groups.
Examples of aryl groups include, but are not limited to, phenyl,
biphenyl, naphthyl, tetrahydronaphthyl, phenylcyclopropyl, and
indanyl. In some embodiments, the aryl group can be a phenyl,
indanyl or naphthyl group. The term "heteroaryl", as well as
derivative terms such as "heteroaryloxy", refers to a 5- or
6-membered aromatic ring containing one or more heteroatoms, viz.,
N, O or S; these heteroaromatic rings may be fused to other
aromatic systems. The aryl or heteroaryl substituents may be
unsubstituted or substituted with one or more chemical moieties.
Examples of suitable substituents include, for example, hydroxy,
nitro, cyano, formyl, C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6
alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.1-C.sub.6 alkoxy,
C.sub.1-C.sub.6 haloalkyl, C.sub.1-C.sub.6 haloalkoxy,
C.sub.1-C.sub.6 acyl, C.sub.1-C.sub.6 alkylthio, C.sub.1-C.sub.6
alkylsulfinyl, C.sub.1-C.sub.6 alkylsulfonyl, C.sub.1-C.sub.6
alkoxycarbonyl, C.sub.1-C.sub.6 carbamoyl, hydroxycarbonyl,
C.sub.1-C.sub.6 alkylcarbonyl, aminocarbonyl, C.sub.1-C.sub.6
alkylaminocarbonyl, C.sub.1-C.sub.6 dialkylaminocarbonyl, provided
that the substituents are sterically compatible and the rules of
chemical bonding and strain energy are satisfied. Preferred
substituents include halogen, C.sub.1-C.sub.2 alkyl and
C.sub.1-C.sub.2 haloalkyl.
[0060] As used herein, the term "alkylcarbonyl" refers to an
unsubstituted or substituted alkyl group bonded to a carbonyl
group. C.sub.1-C.sub.3 alkylcarbonyl and C.sub.1-C.sub.3
haloalkylcarbonyl refer to groups wherein a C.sub.1-C.sub.3
unsubstituted or substituted alkyl or haloalkyl group is bonded to
a carbonyl group (the group contains a total of 2 to 4 carbon
atoms).
[0061] As used herein, the term "alkoxycarbonyl" refers to a group
of the formula
##STR00010##
wherein R is unsubstituted or substituted alkyl.
[0062] As used herein, the term "arylalkyl" refers to an alkyl
group substituted with an unsubstituted or substituted aryl group.
C.sub.7-C.sub.10 arylalkyl refers to a group wherein the total
number of carbon atoms in the group is 7 to 10, not including the
carbon atoms present in any substituents of the aryl group.
[0063] As used herein, the term "alkylamino" refers to an amino
group substituted with one or two unsubstituted or substituted
alkyl groups, which may be the same or different.
[0064] As used herein, the term "haloalkylamino" refers to an
alkylamino group wherein the alkyl carbon atoms are partially or
entirely substituted with halogen atoms.
[0065] As used herein, C.sub.1-C.sub.6 alkylaminocarbonyl refers to
a group of the formula RNHC(O)-- wherein R is C.sub.1-C.sub.6
unsubstituted or substituted alkyl, and C.sub.1-C.sub.6
dialkylaminocarbonyl refers to a group of the formula
R.sub.2NC(O)-- wherein each R is independently C.sub.1-C.sub.6
unsubstituted or substituted alkyl.
[0066] As used herein, the term "alkylcarbamyl" refers to a
carbamyl group substituted on the nitrogen with an unsubstituted or
substituted alkyl group.
[0067] As used herein, the term "alkylsulfonyl" refers to a group
of the formula
##STR00011##
where R is unsubstituted or substituted alkyl.
[0068] As used herein, the term "carbamyl" (also referred to as
carbamoyl and aminocarbonyl) refers to a group of the formula
##STR00012##
[0069] As used herein, the term "dialkylphosphonyl" refers to a
group of the formula
##STR00013##
where R is independently unsubstituted or substituted alkyl in each
occurrence.
[0070] As used herein, C.sub.1-C.sub.6 trialkylsilyl refers to a
group of the formula --SiR.sub.3 wherein each R is independently a
C.sub.1-C.sub.6 unsubstituted or substituted alkyl group (the group
contains a total of 3 to 18 carbon atoms).
[0071] As used herein, Me refers to a methyl group; OMe refers to a
methoxy group; and i-Pr refers to an isopropyl group.
[0072] As used herein, the term "halogen" including derivative
terms such as "halo" refers to fluorine, chlorine, bromine and
iodine.
[0073] As used herein, agriculturally acceptable salts and esters
refer to salts and esters that exhibit herbicidal activity, or that
are or can be converted in plants, water, or soil to the referenced
herbicide. Exemplary agriculturally acceptable esters are those
that are or can be hydrolyzed, oxidized, metabolized, or otherwise
converted, e.g., in plants, water, or soil, to the corresponding
carboxylic acid which, depending on the pH, may be in the
dissociated or undissociated form.
[0074] Compounds described herein can include N-oxides. Pyridine
N-oxides can be obtained by oxidation of the corresponding
pyridines. Suitable oxidation methods are described, for example,
in Houben-Weyl, Methoden der organischen Chemie [Methods in organic
chemistry], expanded and subsequent volumes to the 4th edition,
volume E 7b, p. 565 f
[0075] Pyridine Carboxylic Acid Herbicides
[0076] Compositions and methods of the present disclosure can
include a pyridine carboxylic acid herbicide defined by Formula
(I)
##STR00014##
wherein
[0077] X is N or CY, wherein Y is hydrogen, halogen,
C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 haloalkyl, C.sub.1-C.sub.3
alkoxy, C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio or
C.sub.1-C.sub.3 haloalkylthio;
[0078] R.sup.1 is OR.sup.1' or NR.sup.1''R.sup.1''', wherein
R.sup.1' is hydrogen, C.sub.1-C.sub.8 alkyl, or C.sub.7-C.sub.10
arylalkyl, and R.sup.1'' and R.sup.1''' are independently hydrogen,
C.sub.1-C.sub.12 alkyl, C.sub.3-C.sub.12 alkenyl, or
C.sub.3-C.sub.12 alkynyl;
[0079] R.sup.2 is halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
haloalkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, cyano, or a group of the formula
--CR.sup.17--CR.sup.18--SiR.sup.19R.sup.20R.sup.21, wherein
R.sup.17 is hydrogen, F, or Cl; R.sup.18 is hydrogen, F, Cl,
C.sub.1-C.sub.4 alkyl, or C.sub.1-C.sub.4 haloalkyl; and R.sup.19,
R.sup.20, and R.sup.21 are independently C.sub.1-C.sub.10 alkyl,
C.sub.3-C.sub.6 cycloalkyl, phenyl, substituted phenyl,
C.sub.1-C.sub.10 alkoxy, or OH;
[0080] R.sup.3 and R.sup.4 are independently hydrogen,
C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6
alkenyl, C.sub.3-C.sub.6 haloalkenyl, C.sub.3-C.sub.6 alkynyl,
formyl, C.sub.1-C.sub.3 alkylcarbonyl, C.sub.1-C.sub.3
haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl, C.sub.1-C.sub.6
alkylcarbamyl, C.sub.1-C.sub.6 alkylsulfonyl, C.sub.1-C.sub.6
dialkylphosphonyl, or R.sup.3 and R.sup.4 taken together with N is
a 5- or 6-membered saturated ring, or R.sup.3 and R.sup.4 taken
together represent .dbd.CR.sup.3'(R.sup.4'), wherein R.sup.3' and
R.sup.4' are independently hydrogen, C.sub.1-C.sub.6 alkyl,
C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 alkynyl, C.sub.1-C.sub.6
alkoxy or C.sub.1-C.sub.6 alkylamino, or, R.sup.3' and R.sup.4'
taken together with .dbd.C represent a 5- or 6-membered saturated
ring;
[0081] A is one of groups A1 to A36
##STR00015## ##STR00016## ##STR00017## ##STR00018## ##STR00019##
##STR00020##
[0082] R.sup.5, if applicable to the A group, is hydrogen, halogen,
C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, cyclopropyl,
halocyclopropyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4
haloalkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy,
C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio,
C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino,
C.sub.2-C.sub.4 haloalkylamino, OH, or CN;
[0083] R.sup.6, R.sup.6', and R.sup.6'', if applicable to the A
group, are independently hydrogen, halogen, C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, cyclopropyl, halocyclopropyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3
haloalkoxy, C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino or C.sub.2-C.sub.4
haloalkylamino, OH, CN, or NO.sub.2;
[0084] R.sup.7 and R.sup.7' are independently hydrogen, halogen,
C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, cyclopropyl,
halocyclopropyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4
haloalkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy,
C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio,
C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino,
C.sub.1-C.sub.4 haloalkylamino, or phenyl;
[0085] R.sup.8 is hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6
haloalkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 haloalkenyl,
C.sub.3-C.sub.6 alkynyl, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl,
C.sub.1-C.sub.6 alkylcarbamyl, C.sub.1-C.sub.6 alkylsulfonyl,
C.sub.1-C.sub.6 trialkylsilyl, or phenyl;
[0086] or an agriculturally acceptable N-oxide or salt thereof.
[0087] In some embodiments, R.sup.1 is OR.sup.1', wherein R.sup.1'
is hydrogen, C.sub.1-C.sub.8 alkyl, or C.sub.7-C.sub.10 arylalkyl.
In some embodiments, R.sup.1' is hydrogen or C.sub.1-C.sub.8 alkyl.
In some embodiments, R.sup.1' is hydrogen.
[0088] In some embodiments, R.sup.2 is halogen, C.sub.1-C.sub.4
alkyl, C.sub.1-C.sub.4 haloalkyl, C.sub.2-C.sub.4 alkynyl,
C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.1-C.sub.4-alkoxy, or C.sub.1-C.sub.4 haloalkoxy. In some
embodiments, R.sup.2 is halogen, C.sub.2-C.sub.4-alkenyl,
C.sub.2-C.sub.4 haloalkenyl, or C.sub.1-C.sub.4-alkoxy. In some
embodiments, R.sup.2 is halogen. In some embodiments, R.sup.2 is
C.sub.2-C.sub.4-alkenyl or C.sub.2-C.sub.4 haloalkenyl. In some
embodiments, R.sup.2 is C.sub.1-C.sub.4 alkoxy. In some
embodiments, R.sup.2 is Cl, OMe, vinyl, or 1-propenyl. In some
embodiments, R.sup.2 is Cl. In some embodiments, R.sup.2 is OMe. In
some embodiments, R.sup.2 is vinyl or 1-propenyl.
[0089] In some embodiments, R.sup.3 and R.sup.4 are independently
hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl,
C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 haloalkenyl,
C.sub.3-C.sub.6 alkynyl, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl,
C.sub.1-C.sub.6 alkylcarbamyl, or R.sup.3 and R.sup.4 taken
together represent .dbd.CR.sup.3'(R.sup.4'), wherein R.sup.3' and
R.sup.4' are independently hydrogen, C.sub.1-C.sub.6 alkyl,
C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 alkynyl, C.sub.1-C.sub.6
alkoxy, or C.sub.1-C.sub.6 alkylamino. In some embodiments, R.sup.3
and R.sup.4 are independently hydrogen, C.sub.1-C.sub.6 alkyl,
C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6
haloalkenyl, formyl, C.sub.1-C.sub.3 alkylcarbonyl, C.sub.1-C.sub.3
haloalkylcarbonyl, or R.sup.3 and R.sup.4 taken together represent
.dbd.CR.sup.3'(R.sup.4'), wherein R.sup.3' and R.sup.4' are
independently hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6
alkoxy or C.sub.1-C.sub.6 alkylamino. In some embodiments, R.sup.3
and R.sup.4 are independently hydrogen, C.sub.1-C.sub.6 alkyl,
C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6
haloalkenyl, formyl, C.sub.1-C.sub.3 alkylcarbonyl, or
C.sub.1-C.sub.3 haloalkylcarbonyl. In some embodiments, at least
one of R.sup.3 and R.sup.4 are hydrogen. In some embodiments,
R.sup.3 and R.sup.4 are both hydrogen.
[0090] In some embodiments, X is N, CH or CF. In some embodiments,
X is N. In some embodiments, X is CH. In some embodiments, X is CF.
In other embodiments, X is C--CH.sub.3.
[0091] In some embodiments, A is A1, A2, A3, A4, A5, A6, A7, A8,
A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, A19, or A20. In
other embodiments, A is one of A21, A22, A23, A24, A25, A26, A27,
A28, A29, A30, A31, A32, A33, A34, A35, and A36.
[0092] In some embodiments, A is one of groups A1, A2, A3, A7, A8,
A9, A10, A13, A14, and A15. In some embodiments, A is one of groups
A1, A2, A3, A13, A14, and A15. In some embodiments, A is one of
groups A13, A14, and A15. In some embodiments, A is A15.
[0093] In some embodiments, R.sup.5 is hydrogen, halogen,
C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, C.sub.1-C.sub.3
alkoxy, C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio,
C.sub.1-C.sub.3 haloalkylthio, or amino. In some embodiments,
R.sup.5 is hydrogen, halogen, C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3
haloalkoxy, or amino. In some embodiments, R.sup.5 is hydrogen,
halogen, C.sub.1-C.sub.4 alkyl or C.sub.1-C.sub.4 alkoxy. In some
embodiments, R.sup.5 is hydrogen or F. In some embodiments, R.sup.5
is hydrogen. In other embodiments, R.sup.5 is F.
[0094] In some embodiments, R.sup.6 is hydrogen, halogen,
C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, C.sub.1-C.sub.3
alkoxy, or C.sub.1-C.sub.3 haloalkoxy. In some embodiments, R.sup.6
is hydrogen or fluorine. In some embodiments, R.sup.6 is hydrogen.
In some embodiments, R.sup.6 is fluorine.
[0095] In some embodiments, R.sup.6' is hydrogen or halogen. In
some embodiments, R.sup.6' is hydrogen, F, or Cl. In some
embodiments, R.sup.6' is hydrogen or F. In some embodiments,
R.sup.6' is hydrogen.
[0096] In some embodiments, R.sup.6'' is hydrogen, halogen,
C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, cyclopropyl,
C.sub.2-C.sub.4 alkynyl, CN, or NO.sub.2. In some embodiments,
R.sup.6'' is hydrogen. In some embodiments, R.sup.6'' is halogen.
In some embodiments, R.sup.6'' is C.sub.1-C.sub.4 alkyl. In some
embodiments, R.sup.6'' is C.sub.1-C.sub.4 haloalkyl. In some
embodiments, R.sup.6'' is cyclopropyl. In some embodiments,
R.sup.6'' is C.sub.2-C.sub.4 alkynyl. In some embodiments,
R.sup.6'' is CN. In some embodiments, R.sup.6'' is NO.sub.2.
[0097] In some embodiments:
[0098] X is N, CH, CF, CCl, or CBr;
[0099] R.sup.1 is OR.sup.1', wherein R.sup.1' is hydrogen or
C.sub.1-C.sub.4 alkyl;
[0100] R.sup.2 is chlorine;
[0101] R.sup.3 and R.sup.4 are hydrogen;
[0102] A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13,
A14, A15, A16, A17, A18, A19, or A20;
[0103] R.sup.5 is hydrogen, halogen, OH, amino, CN, C.sub.1-C.sub.3
alkyl, C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3 alkylamino, or
cyclopropyl;
[0104] R.sup.6, R.sup.6', and R.sup.6'' are independently hydrogen,
halogen, OH, NH.sub.2, CN, C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3
alkoxy, cyclopropyl, or vinyl;
[0105] R.sup.7 and R.sup.7' are independently hydrogen, halogen,
C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3
alkylthio, cyclopropyl, or C.sub.1-C.sub.3 alkylamino, or phenyl;
and
[0106] R.sup.8 is hydrogen, C.sub.1-C.sub.3 alkyl, phenyl, or
C.sub.1-C.sub.3 alkylcarbonyl.
[0107] In some embodiments, R.sup.2 is halogen,
C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4 haloalkenyl, or
C.sub.1-C.sub.4-alkoxy; R.sup.3 and R.sup.4 are both hydrogen; and
X is N, CH, or CF.
[0108] In some embodiments, R.sup.2 is halogen; R.sup.3 and R.sup.4
are both hydrogen; and X is N, CH, or CF.
[0109] In some embodiments, R.sup.2 is C.sub.2-C.sub.4-alkenyl or
C.sub.2-C.sub.4 haloalkenyl; R.sup.3 and R.sup.4 are both hydrogen;
and X is N, CH, or CF.
[0110] In some embodiments, R.sup.2 is C.sub.1-C.sub.4-alkoxy;
R.sup.3 and R.sup.4 are both hydrogen; and X is N, CH, or CF.
[0111] In some embodiments, R.sup.2 is halogen,
C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4 haloalkenyl, or
C.sub.1-C.sub.4-alkoxy; R.sup.3 and R.sup.4 are both hydrogen; X is
N, CH, or CF; R.sup.5 is hydrogen or F; R.sup.6 is hydrogen or F;
R.sup.6' is hydrogen; R.sup.6'', if applicable to the relevant A
group, is hydrogen or halogen; and R.sup.7 and R.sup.7', if
applicable to the relevant A group, are independently hydrogen or
halogen.
[0112] In some embodiments, R.sup.2 is halogen,
C.sub.1-C.sub.4-alkoxy, or C.sub.2-C.sub.4-alkenyl; R.sup.3 and
R.sup.4 are hydrogen; X is N, CH, or CF; and A is one of groups A1
to A20.
[0113] In some embodiments, R.sup.2 is chlorine; R.sup.3 and
R.sup.4 are hydrogen; X is N, CH, or CF; A is one of groups A1 to
A20; R.sup.5 is hydrogen or F; R.sup.6 and R.sup.6' are
independently hydrogen or F; and R.sup.7 and R.sup.7', if
applicable to the relevant A group, are independently hydrogen,
halogen, C.sub.1-C.sub.4 alkyl, or C.sub.1-C.sub.4 haloalkyl.
[0114] In some embodiments, R.sup.2 is chlorine, methoxy, vinyl, or
1-propenyl; R.sup.3 and R.sup.4 are hydrogen; and X is N, CH, or
CF.
[0115] In some embodiments, R.sup.2 is chlorine; R.sup.3 and
R.sup.4 are hydrogen; and X is N, CH, or CF.
[0116] In some embodiments, R.sup.2 is vinyl or 1-propenyl; R.sup.3
and R.sup.4 are hydrogen; and X is N, CH, or CF.
[0117] In some embodiments, R.sup.2 is methoxy; R.sup.3 and R.sup.4
are hydrogen; and X is N, CH, or CF.
[0118] In some embodiments, R.sup.2 is chlorine; R.sup.3 and
R.sup.4 are hydrogen; and X is N.
[0119] In some embodiments, R.sup.2 is chlorine; R.sup.3 and
R.sup.4 are hydrogen; and X is CH.
[0120] In some embodiments, R.sup.2 is chlorine; R.sup.3 and
R.sup.4 are hydrogen; and X is CF.
[0121] In some embodiments, R.sup.2 is chlorine; R.sup.3 and
R.sup.4 are hydrogen; X is CF; A is one of A1, A2, A3, A7, A8, A9,
A10, A13, A14, or A15; R.sup.5 is F; and R.sup.6 is H.
[0122] In some embodiments, R.sup.2 is chlorine, methoxy, vinyl, or
1-propenyl; R.sup.3 and R.sup.4 are hydrogen; X is N, CH, or CF;
and A is one of A21-A36.
[0123] In some embodiments, R.sup.2 is chlorine, methoxy, vinyl, or
1-propenyl; R.sup.3 and R.sup.4 are hydrogen; X is CF; and A is one
of
##STR00021##
wherein R.sup.5 is hydrogen or F.
[0124] In some embodiments, R.sup.2 is chlorine, methoxy, vinyl, or
1-propenyl; R.sup.3 and R.sup.4 are hydrogen; X is N, CH, or CF;
and A is
##STR00022##
where R.sup.5 is hydrogen or F.
[0125] In some embodiments, R.sup.2 is chlorine, methoxy, vinyl, or
1-propenyl; R.sup.3 and R.sup.4 are hydrogen; X is N, CH, or CF;
and A is
##STR00023##
[0126] In some embodiments, R.sup.2 is chlorine, methoxy, vinyl, or
1-propenyl; R.sup.3 and R.sup.4 are hydrogen; X is CF; and A is
##STR00024##
[0127] In some embodiments, the pyridine carboxylic acid herbicide
is a compound defined by Formula (I)
##STR00025##
wherein
[0128] X is N or CY, wherein Y is hydrogen, halogen,
C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 haloalkyl, C.sub.1-C.sub.3
alkoxy, C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio, or
C.sub.1-C.sub.3 haloalkylthio;
[0129] R.sup.1 is OR.sup.1' or NR.sup.1''R.sup.1''' wherein is
hydrogen, C.sub.1-C.sub.3 alkyl, or C.sub.7-C.sub.10 arylalkyl, and
R.sup.1'' and R.sup.1''' are independently hydrogen,
C.sub.1-C.sub.12 alkyl, C.sub.3-C.sub.12 alkenyl, or
C.sub.3-C.sub.12 alkynyl;
[0130] R.sup.2 is halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
haloalkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, cyano, or a group of the formula
--CR.sup.17.dbd.CR.sup.18--SiR.sup.19R.sup.20R.sup.21, wherein
R.sup.17 is hydrogen, F, or Cl; R.sup.18 is hydrogen, F, Cl,
C.sub.1-C.sub.4 alkyl, or C.sub.1-C.sub.4 haloalkyl; and R.sup.19,
R.sup.20, and R.sup.21 are independently C.sub.1-C.sub.10 alkyl,
C.sub.3-C.sub.6 cycloalkyl, phenyl, substituted phenyl,
C.sub.1-C.sub.10 alkoxy, or OH;
[0131] R.sup.3 and R.sup.4 are independently hydrogen,
C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6
alkenyl, C.sub.3-C.sub.6 haloalkenyl, C.sub.3-C.sub.6 alkynyl,
formyl, C.sub.1-C.sub.3 alkylcarbonyl, C.sub.1-C.sub.3
haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl, C.sub.1-C.sub.6
alkylcarbamyl, C.sub.1-C.sub.6 alkylsulfonyl, C.sub.1-C.sub.6
trialkylsilyl, C.sub.1-C.sub.6 dialkylphosphonyl, or R.sup.3 and
R.sup.4 taken together with N is a 5- or 6-membered saturated ring,
or R.sup.3 and R.sup.4 taken together represent
.dbd.CR.sup.3'(R.sup.4'), wherein R.sup.3' and R.sup.4' are
independently hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.3-C.sub.6
alkenyl, C.sub.3-C.sub.6 alkynyl, C.sub.1-C.sub.6 alkoxy or
C.sub.1-C.sub.6 alkylamino, or, R.sup.3' and R.sup.4' taken
together with .dbd.C represent a 5- or 6-membered saturated
ring;
[0132] A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13,
A14, A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26,
A27, A28, A29, A30, A31, A32, A33, A34, A35, or A36;
[0133] R.sup.5 is hydrogen, halogen, C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, cyclopropyl, halocyclopropyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3
haloalkoxy, C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, OH, or CN;
[0134] R.sup.6, R.sup.6', and R.sup.6'' are independently hydrogen,
halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl,
cyclopropyl, halocyclopropyl, C.sub.2-C.sub.4 alkenyl,
C.sub.2-C.sub.4 haloalkenyl, C.sub.2-C.sub.4 alkynyl,
C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3
alkylthio, C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4
alkylamino or C.sub.2-C.sub.4 haloalkylamino, OH, CN, or
NO.sub.2;
[0135] R.sup.7 and R.sup.7' are independently hydrogen, halogen,
C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, cyclopropyl,
halocyclopropyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4
haloalkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy,
C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio,
C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino,
C.sub.2-C.sub.4 haloalkylamino, or phenyl; and
[0136] R.sup.8 is hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6
haloalkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 haloalkenyl,
C.sub.3-C.sub.6 alkynyl, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl,
C.sub.1-C.sub.6 alkylcarbamyl, C.sub.1-C.sub.6 alkylsulfonyl,
C.sub.1-C.sub.6 trialkylsilyl, or phenyl;
[0137] or an agriculturally acceptable N-oxide or salt thereof,
[0138] with the proviso that the pyridine carboxylic acid herbicide
is not a compound defined by Formula (I)
##STR00026##
wherein
[0139] X is N, CH, CF, CCl, or CBr;
[0140] R.sup.1 is OR.sup.1', wherein R.sup.1' is hydrogen or
C.sub.1-C.sub.4 alkyl;
[0141] R.sup.2 is chlorine;
[0142] R.sup.3 and R.sup.4 are hydrogen;
[0143] A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13,
A14, A15, A16, A17, A18, A19, or A20;
[0144] R.sup.5 is hydrogen, halogen, OH, amino, CN, C.sub.1-C.sub.3
alkyl, C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3 alkylamino, or
cyclopropyl;
[0145] R.sup.6, R.sup.6', and R.sup.6'' are independently hydrogen,
halogen, OH, NH.sub.2, CN, C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3
alkoxy, cyclopropyl, or vinyl;
[0146] R.sup.7 and R.sup.7' are independently hydrogen, halogen,
C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3
alkylthio, cyclopropyl, C.sub.1-C.sub.3 alkylamino, or phenyl;
and
[0147] R.sup.8 is hydrogen, C.sub.1-C.sub.3 alkyl, phenyl, or
C.sub.1-C.sub.3 alkylcarbonyl;
or an agriculturally acceptable N-oxide or salt thereof.
[0148] In some of these embodiments, R.sup.1 is OR.sup.1. In some
of these embodiments, X is CF. In some of these embodiments, A is
A15. In some of these embodiments, R.sup.5 is F.
[0149] In some embodiments:
[0150] X is CY, wherein Y is C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3
haloalkyl, C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3 haloalkoxy,
C.sub.1-C.sub.3 alkylthio, or C.sub.1-C.sub.3 haloalkylthio;
[0151] R.sup.1 is OR.sup.1' or NR.sup.1''R.sup.1''' wherein
R.sup.1' is hydrogen, C.sub.1-C.sub.8 alkyl, or C.sub.7-C.sub.10
arylalkyl, and R.sup.1'' and R.sup.1''' are independently hydrogen,
C.sub.1-C.sub.12 alkyl, C.sub.3-C.sub.12 alkenyl, or
C.sub.3-C.sub.12 alkynyl;
[0152] R.sup.2 is halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
haloalkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, cyano, or a group of the formula
--CR.sup.17.dbd.CR.sup.18--SiR.sup.19R.sup.20R.sup.21, wherein
R.sup.17 is hydrogen, F, or Cl; R.sup.18 is hydrogen, F, Cl,
C.sub.1-C.sub.4 alkyl, or C.sub.1-C.sub.4 haloalkyl; and R.sup.19,
R.sup.20, and R.sup.21 are independently C.sub.1-C.sub.10 alkyl,
C.sub.3-C.sub.6 cycloalkyl, phenyl, substituted phenyl,
C.sub.1-C.sub.10 alkoxy, or OH;
[0153] R.sup.3 and R.sup.4 are independently hydrogen,
C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6
alkenyl, C.sub.3-C.sub.6 haloalkenyl, C.sub.3-C.sub.6 alkynyl,
formyl, C.sub.1-C.sub.3 alkylcarbonyl, C.sub.1-C.sub.3
haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl, C.sub.1-C.sub.6
alkylcarbamyl, C.sub.1-C.sub.6 alkylsulfonyl, C.sub.1-C.sub.6
trialkylsilyl, C.sub.1-C.sub.6 dialkylphosphonyl, or R.sup.3 and
R.sup.4 taken together with N is a 5- or 6-membered saturated ring,
or R.sup.3 and R.sup.4 taken together represent
.dbd.CR.sup.3'(R.sup.4'), wherein R.sup.3' and R.sup.4' are
independently hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.3-C.sub.6
alkenyl, C.sub.3-C.sub.6 alkynyl, C.sub.1-C.sub.6 alkoxy or
C.sub.1-C.sub.6 alkylamino, or, R.sup.3' and R.sup.4' taken
together with .dbd.C represent a 5- or 6-membered saturated
ring;
[0154] A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13,
A14, A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26,
A27, A28, A29, A30, A31, A32, A33, A34, A35, or A36;
[0155] R.sup.5 is hydrogen, halogen, C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, cyclopropyl, halocyclopropyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3
haloalkoxy, C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, OH, or CN;
[0156] R.sup.6, R.sup.6', and R.sup.6'' are independently hydrogen,
halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl,
cyclopropyl, halocyclopropyl, C.sub.2-C.sub.4 alkenyl,
C.sub.2-C.sub.4 haloalkenyl, C.sub.2-C.sub.4 alkynyl,
C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3
alkylthio, C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4
alkylamino or C.sub.2-C.sub.4 haloalkylamino, OH, CN, or
NO.sub.2;
[0157] R.sup.7 and R.sup.7' are independently hydrogen, halogen,
C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, cyclopropyl,
halocyclopropyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4
haloalkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy,
C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio,
C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino,
C.sub.2-C.sub.4 haloalkylamino, or phenyl; and
[0158] R.sup.8 is hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6
haloalkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 haloalkenyl,
C.sub.3-C.sub.6 alkynyl, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl,
C.sub.1-C.sub.6 alkylcarbamyl, C.sub.1-C.sub.6 alkylsulfonyl,
C.sub.1-C.sub.6 trialkylsilyl, or phenyl.
[0159] In some of these embodiments, R.sup.1 is OR.sup.1. In some
of these embodiments, A is A15. In some of these embodiments,
R.sup.5 is F.
[0160] In some embodiments:
[0161] X is N or CY, wherein Y is hydrogen, halogen,
C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 haloalkyl, C.sub.1-C.sub.3
alkoxy, C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio, or
C.sub.1-C.sub.3 haloalkylthio;
[0162] R.sup.1 is OR.sup.1' or NR.sup.1''R.sup.1''', wherein
R.sup.1' is C.sub.1-C.sub.8 alkyl, or C.sub.7-C.sub.10 arylalkyl,
and R.sup.1'' and R.sup.1''' are independently hydrogen,
C.sub.1-C.sub.12 alkyl, C.sub.3-C.sub.12 alkenyl, or
C.sub.3-C.sub.12 alkynyl;
[0163] R.sup.2 is halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
haloalkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, cyano, or a group of the formula
--CR.sup.17.dbd.CR.sup.18--SiR.sup.19R.sup.20R.sup.21, wherein
R.sup.17 is hydrogen, F, or Cl; R.sup.18 is hydrogen, F, Cl,
C.sub.1-C.sub.4 alkyl, or C.sub.1-C.sub.4 haloalkyl; and R.sup.19,
R.sup.20, and R.sup.21 are independently C.sub.1-C.sub.10 alkyl,
C.sub.3-C.sub.6 cycloalkyl, phenyl, substituted phenyl,
C.sub.1-C.sub.10 alkoxy, or OH;
[0164] R.sup.3 and R.sup.4 are independently hydrogen,
C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6
alkenyl, C.sub.3-C.sub.6 haloalkenyl, C.sub.3-C.sub.6 alkynyl,
formyl, C.sub.1-C.sub.3 alkylcarbonyl, C.sub.1-C.sub.3
haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl, C.sub.1-C.sub.6
alkylcarbamyl, C.sub.1-C.sub.6 alkylsulfonyl, C.sub.1-C.sub.6
trialkylsilyl, C.sub.1-C.sub.6 dialkylphosphonyl, or R.sup.3 and
R.sup.4 taken together with N is a 5- or 6-membered saturated ring,
or R.sup.3 and R.sup.4 taken together represent
.dbd.CR.sup.3'(R.sup.4'), wherein R.sup.3' and R.sup.4' are
independently hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.3-C.sub.6
alkenyl, C.sub.3-C.sub.6 alkynyl, C.sub.1-C.sub.6 alkoxy or
C.sub.1-C.sub.6 alkylamino, or, R.sup.3' and R.sup.4' taken
together with .dbd.C represent a 5- or 6-membered saturated
ring;
[0165] A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13,
A14, A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26,
A27, A28, A29, A30, A31, A32, A33, A34, A35, or A36;
[0166] R.sup.5 is hydrogen, halogen, C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, cyclopropyl, halocyclopropyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3
haloalkoxy, C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, OH, or CN;
[0167] R.sup.6, R.sup.6', and R.sup.6'' are independently hydrogen,
halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl,
cyclopropyl, halocyclopropyl, C.sub.2-C.sub.4 alkenyl,
C.sub.2-C.sub.4 haloalkenyl, C.sub.2-C.sub.4 alkynyl,
C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3
alkylthio, C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4
alkylamino or C.sub.2-C.sub.4 haloalkylamino, OH, CN, or
NO.sub.2;
[0168] R.sup.7 and R.sup.7' are independently hydrogen, halogen,
C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, cyclopropyl,
halocyclopropyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4
haloalkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy,
C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio,
C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino,
C.sub.2-C.sub.4 haloalkylamino, or phenyl;
[0169] R.sup.8 is hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6
haloalkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 haloalkenyl,
C.sub.3-C.sub.6 alkynyl, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl,
C.sub.1-C.sub.6 alkylcarbamyl, C.sub.1-C.sub.6 alkylsulfonyl,
C.sub.1-C.sub.6 trialkylsilyl, or phenyl;
[0170] In some of these embodiments, R.sup.1 is OR.sup.1. In some
of these embodiments, X is CF. In some of these embodiments, A is
A15. In some of these embodiments, R.sup.5 is F.
[0171] In some embodiments:
[0172] X is N or CY, wherein Y is hydrogen, halogen,
C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 haloalkyl, C.sub.1-C.sub.3
alkoxy, C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio, or
C.sub.1-C.sub.3 haloalkylthio;
[0173] R.sup.1 is OR.sup.1' or NR.sup.1''R.sup.1''', wherein
R.sup.1' is hydrogen, C.sub.1-C.sub.8 alkyl, or C.sub.7-C.sub.10
arylalkyl, and R.sup.1'' and R.sup.1''' are independently hydrogen,
C.sub.1-C.sub.12 alkyl, C.sub.3-C.sub.12 alkenyl, or
C.sub.3-C.sub.12 alkynyl;
[0174] R.sup.2 is F, Br, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
haloalkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, cyano, or a group of the formula
--CR.sup.17.dbd.CR.sup.18--SiR.sup.19R.sup.20R.sup.21, wherein
R.sup.17 is hydrogen, F, or Cl; R.sup.18 is hydrogen, F, Cl,
C.sub.1-C.sub.4 alkyl, or C.sub.1-C.sub.4 haloalkyl; and R.sup.19,
R.sup.20, and R.sup.21 are independently C.sub.1-C.sub.10 alkyl,
C.sub.3-C.sub.6 cycloalkyl, phenyl, substituted phenyl,
C.sub.1-C.sub.10 alkoxy, or OH;
[0175] R.sup.3 and R.sup.4 are independently hydrogen,
C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6
alkenyl, C.sub.3-C.sub.6 haloalkenyl, C.sub.3-C.sub.6 alkynyl,
formyl, C.sub.1-C.sub.3 alkylcarbonyl, C.sub.1-C.sub.3
haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl, C.sub.1-C.sub.6
alkylcarbamyl, C.sub.1-C.sub.6 alkylsulfonyl, C.sub.1-C.sub.6
trialkylsilyl, C.sub.1-C.sub.6 dialkylphosphonyl, or R.sup.3 and
R.sup.4 taken together with N is a 5- or 6-membered saturated ring,
or R.sup.3 and R.sup.4 taken together represent
.dbd.CR.sup.3'(R.sup.4'), wherein R.sup.3' and R.sup.4' are
independently hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.3-C.sub.6
alkenyl, C.sub.3-C.sub.6 alkynyl, C.sub.1-C.sub.6 alkoxy or
C.sub.1-C.sub.6 alkylamino, or, R.sup.3' and R.sup.4' taken
together with .dbd.C represent a 5- or 6-membered saturated
ring;
[0176] A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13,
A14, A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26,
A27, A28, A29, A30, A31, A32, A33, A34, A35, or A36;
[0177] R.sup.5 is hydrogen, halogen, C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, cyclopropyl, halocyclopropyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3
haloalkoxy, C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, OH, or CN;
[0178] R.sup.6, R.sup.6', and R.sup.6'' are independently hydrogen,
halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl,
cyclopropyl, halocyclopropyl, C.sub.2-C.sub.4 alkenyl,
C.sub.2-C.sub.4 haloalkenyl, C.sub.2-C.sub.4 alkynyl,
C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3
alkylthio, C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4
alkylamino or C.sub.2-C.sub.4 haloalkylamino, OH, CN, or
NO.sub.2;
[0179] R.sup.7 and R.sup.7' are independently hydrogen, halogen,
C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, cyclopropyl,
halocyclopropyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4
haloalkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy,
C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio,
C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino,
C.sub.2-C.sub.4 haloalkylamino, or phenyl; and
[0180] R.sup.8 is hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6
haloalkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 haloalkenyl,
C.sub.3-C.sub.6 alkynyl, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl,
C.sub.1-C.sub.6 alkylcarbamyl, C.sub.1-C.sub.6 alkylsulfonyl,
C.sub.1-C.sub.6 trialkylsilyl, or phenyl.
[0181] In some of these embodiments, R.sup.1 is OR.sup.1. In some
of these embodiments, X is CF. In some of these embodiments, A is
A15. In some of these embodiments, R.sup.5 is F.
[0182] In some embodiments:
[0183] X is N or CY, wherein Y is hydrogen, halogen,
C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 haloalkyl, C.sub.1-C.sub.3
alkoxy, C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio, or
C.sub.1-C.sub.3 haloalkylthio;
[0184] R.sup.1 is OR.sup.1' or NR.sup.1''R.sup.1''', wherein
R.sup.1' is hydrogen, C.sub.1-C.sub.8 alkyl, or C.sub.7-C.sub.10
arylalkyl, and R.sup.1'' and R.sup.1''' are independently hydrogen,
C.sub.1-C.sub.12 alkyl, C.sub.3-C.sub.12 alkenyl, or
C.sub.3-C.sub.12 alkynyl;
[0185] R.sup.2 is halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
haloalkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, cyano, or a group of the formula
--CR.sup.17.dbd.CR.sup.18--SiR.sup.19R.sup.20R.sup.21, wherein
R.sup.17 is hydrogen, F, or Cl; R.sup.18 is hydrogen, F, Cl,
C.sub.1-C.sub.4 alkyl, or C.sub.1-C.sub.4 haloalkyl; and R.sup.19,
R.sup.20, and R.sup.21 are independently C.sub.1-C.sub.10 alkyl,
C.sub.3-C.sub.6 cycloalkyl, phenyl, substituted phenyl,
C.sub.1-C.sub.10 alkoxy, or OH;
[0186] R.sup.3 and R.sup.4 are independently C.sub.1-C.sub.6 alkyl,
C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6
haloalkenyl, C.sub.3-C.sub.6 alkynyl, formyl, C.sub.1-C.sub.3
alkylcarbonyl, C.sub.1-C.sub.3 haloalkylcarbonyl, C.sub.1-C.sub.6
alkoxycarbonyl, C.sub.1-C.sub.6 alkylcarbamyl, C.sub.1-C.sub.6
alkylsulfonyl, C.sub.1-C.sub.6 trialkylsilyl, C.sub.1-C.sub.6
dialkylphosphonyl, or R.sup.3 and R.sup.4 taken together with N is
a 5- or 6-membered saturated ring, or R.sup.3 and R.sup.4 taken
together represent .dbd.CR.sup.3'(R.sup.4'), wherein R.sup.3' and
R.sup.4' are independently hydrogen, C.sub.1-C.sub.6 alkyl,
C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 alkynyl, C.sub.1-C.sub.6
alkoxy or C.sub.1-C.sub.6 alkylamino, or, R.sup.3' and R.sup.4'
taken together with .dbd.C represent a 5- or 6-membered saturated
ring;
[0187] A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13,
A14, A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26,
A27, A28, A29, A30, A31, A32, A33, A34, A35, or A36;
[0188] R.sup.5 is hydrogen, halogen, C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, cyclopropyl, halocyclopropyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3
haloalkoxy, C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, OH, or CN;
[0189] R.sup.6, R.sup.6', and R.sup.6'' are independently hydrogen,
halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl,
cyclopropyl, halocyclopropyl, C.sub.2-C.sub.4 alkenyl,
C.sub.2-C.sub.4 haloalkenyl, C.sub.2-C.sub.4 alkynyl,
C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3
alkylthio, C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4
alkylamino or C.sub.2-C.sub.4 haloalkylamino, OH, CN, or
NO.sub.2;
[0190] R.sup.7 and R.sup.7' are independently hydrogen, halogen,
C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, cyclopropyl,
halocyclopropyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4
haloalkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy,
C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio,
C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino,
C.sub.2-C.sub.4 haloalkylamino, or phenyl; and
[0191] R.sup.8 is hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6
haloalkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 haloalkenyl,
C.sub.3-C.sub.6 alkynyl, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl,
C.sub.1-C.sub.6 alkylcarbamyl, C.sub.1-C.sub.6 alkylsulfonyl,
C.sub.1-C.sub.6 trialkylsilyl, or phenyl.
[0192] In some of these embodiments, R.sup.1 is OR.sup.1. In some
of these embodiments, X is CF. In some of these embodiments, A is
A15. In some of these embodiments, R.sup.5 is F.
[0193] In some embodiments:
[0194] X is N or CY, wherein Y is hydrogen, halogen,
C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 haloalkyl, C.sub.1-C.sub.3
alkoxy, C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio, or
C.sub.1-C.sub.3 haloalkylthio;
[0195] R.sup.1 is OR.sup.1' or NR.sup.1''R.sup.1''', wherein
R.sup.1' is hydrogen, C.sub.1-C.sub.8 alkyl, or C.sub.7-C.sub.10
arylalkyl, and R.sup.1'' and R.sup.1''' are independently hydrogen,
C.sub.1-C.sub.12 alkyl, C.sub.3-C.sub.12 alkenyl, or
C.sub.3-C.sub.12 alkynyl;
[0196] R.sup.2 is halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
haloalkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, cyano, or a group of the formula
--CR.sup.17.dbd.CR.sup.18--SiR.sup.19R.sup.20R.sup.21, wherein
R.sup.17 is hydrogen, F, or Cl; R.sup.18 is hydrogen, F, Cl,
C.sub.1-C.sub.4 alkyl, or C.sub.1-C.sub.4 haloalkyl; and R.sup.19,
R.sup.20, and R.sup.21 are independently C.sub.1-C.sub.10 alkyl,
C.sub.3-C.sub.6 cycloalkyl, phenyl, substituted phenyl,
C.sub.1-C.sub.10 alkoxy, or OH;
[0197] R.sup.3 and R.sup.4 are independently hydrogen,
C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6
alkenyl, C.sub.3-C.sub.6 haloalkenyl, C.sub.3-C.sub.6 alkynyl,
formyl, C.sub.1-C.sub.3 alkylcarbonyl, C.sub.1-C.sub.3
haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl, C.sub.1-C.sub.6
alkylcarbamyl, C.sub.1-C.sub.6 alkylsulfonyl, C.sub.1-C.sub.6
trialkylsilyl, C.sub.1-C.sub.6 dialkylphosphonyl, or R.sup.3 and
R.sup.4 taken together with N is a 5- or 6-membered saturated ring,
or R.sup.3 and R.sup.4 taken together represent
.dbd.CR.sup.3'(R.sup.4'), wherein R.sup.3' and R.sup.4' are
independently hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.3-C.sub.6
alkenyl, C.sub.3-C.sub.6 alkynyl, C.sub.1-C.sub.6 alkoxy or
C.sub.1-C.sub.6 alkylamino, or, R.sup.3' and R.sup.4' taken
together with .dbd.C represent a 5- or 6-membered saturated
ring;
[0198] A is A21, A22, A23, A24, A25, A26, A27, A28, A29, A30, A31,
A32, A33, A34, A35, or A36;
[0199] R.sup.5 is hydrogen, halogen, C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, cyclopropyl, halocyclopropyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3
haloalkoxy, C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, OH, or CN;
[0200] R.sup.6, R.sup.6', and R.sup.6'' are independently hydrogen,
halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl,
cyclopropyl, halocyclopropyl, C.sub.2-C.sub.4 alkenyl,
C.sub.2-C.sub.4 haloalkenyl, C.sub.2-C.sub.4 alkynyl,
C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3
alkylthio, C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4
alkylamino or C.sub.2-C.sub.4 haloalkylamino, OH, CN, or
NO.sub.2;
[0201] R.sup.7 and R.sup.7' are independently hydrogen, halogen,
C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, cyclopropyl,
halocyclopropyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4
haloalkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy,
C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio,
C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino,
C.sub.2-C.sub.4 haloalkylamino, or phenyl; and
[0202] R.sup.8 is hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6
haloalkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 haloalkenyl,
C.sub.3-C.sub.6 alkynyl, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl,
C.sub.1-C.sub.6 alkylcarbamyl, C.sub.1-C.sub.6 alkylsulfonyl,
C.sub.1-C.sub.6 trialkylsilyl, or phenyl.
[0203] In some of these embodiments, R.sup.1 is OR.sup.1. In some
of these embodiments, X is CF. In some of these embodiments,
R.sup.5 is F.
[0204] In some embodiments:
[0205] X is N or CY, wherein Y is hydrogen, halogen,
C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 haloalkyl, C.sub.1-C.sub.3
alkoxy, C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio, or
C.sub.1-C.sub.3 haloalkylthio;
[0206] R.sup.1 is OR.sup.1' or NR.sup.1''R.sup.1''', wherein
R.sup.1' is hydrogen, C.sub.1-C.sub.8 alkyl, or C.sub.7-C.sub.10
arylalkyl, and R.sup.1'' and R.sup.1''' are independently hydrogen,
C.sub.1-C.sub.12 alkyl, C.sub.3-C.sub.12 alkenyl, or
C.sub.3-C.sub.12 alkynyl;
[0207] R.sup.2 is halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
haloalkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, cyano, or a group of the formula
--CR.sup.17.dbd.CR.sup.18--SiR.sup.19R.sup.20R.sup.21, wherein
R.sup.17 is hydrogen, F, or Cl; R.sup.18 is hydrogen, F, Cl,
C.sub.1-C.sub.4 alkyl, or C.sub.1-C.sub.4 haloalkyl; and R.sup.19,
R.sup.20, and R.sup.21 are independently C.sub.1-C.sub.10 alkyl,
C.sub.3-C.sub.6 cycloalkyl, phenyl, substituted phenyl,
C.sub.1-C.sub.10 alkoxy, or OH;
[0208] R.sup.3 and R.sup.4 are independently hydrogen,
C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6
alkenyl, C.sub.3-C.sub.6 haloalkenyl, C.sub.3-C.sub.6 alkynyl,
formyl, C.sub.1-C.sub.3 alkylcarbonyl, C.sub.1-C.sub.3
haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl, C.sub.1-C.sub.6
alkylcarbamyl, C.sub.1-C.sub.6 alkylsulfonyl, C.sub.1-C.sub.6
trialkylsilyl, C.sub.1-C.sub.6 dialkylphosphonyl, or R.sup.3 and
R.sup.4 taken together with N is a 5- or 6-membered saturated ring,
or R.sup.3 and R.sup.4 taken together represent
.dbd.CR.sup.3'(R.sup.4'), wherein R.sup.3' and R.sup.4' are
independently hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.3-C.sub.6
alkenyl, C.sub.3-C.sub.6 alkynyl, C.sub.1-C.sub.6 alkoxy or
C.sub.1-C.sub.6 alkylamino, or, R.sup.3' and R.sup.4' taken
together with .dbd.C represent a 5- or 6-membered saturated
ring;
[0209] A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13,
A14, A15, A16, A17, A18, A19, or A20;
[0210] R.sup.5 is C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl,
halocyclopropyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4
haloalkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 haloalkoxy,
C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3 haloalkylthio,
C.sub.2-C.sub.4 alkylamino, or C.sub.2-C.sub.4 haloalkylamino;
[0211] R.sup.6, R.sup.6', and R.sup.6'' are independently hydrogen,
halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl,
cyclopropyl, halocyclopropyl, C.sub.2-C.sub.4 alkenyl,
C.sub.2-C.sub.4 haloalkenyl, C.sub.2-C.sub.4 alkynyl,
C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3
alkylthio, C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4
alkylamino or C.sub.2-C.sub.4 haloalkylamino, OH, CN, or
NO.sub.2;
[0212] R.sup.7 and R.sup.7' are independently hydrogen, halogen,
C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, cyclopropyl,
halocyclopropyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4
haloalkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy,
C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio,
C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino,
C.sub.2-C.sub.4 haloalkylamino, or phenyl; and
[0213] R.sup.8 is hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6
haloalkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 haloalkenyl,
C.sub.3-C.sub.6 alkynyl, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl,
C.sub.1-C.sub.6 alkylcarbamyl, C.sub.1-C.sub.6 alkylsulfonyl,
C.sub.1-C.sub.6 trialkylsilyl, or phenyl.
[0214] In some of these embodiments, R.sup.1 is OR.sup.1. In some
of these embodiments, X is CF. In some of these embodiments, A is
A15. In some of these embodiments, R.sup.5 is F.
[0215] In some embodiments:
[0216] X is N or CY, wherein Y is hydrogen, halogen,
C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 haloalkyl, C.sub.1-C.sub.3
alkoxy, C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio, or
C.sub.1-C.sub.3 haloalkylthio;
[0217] R.sup.1 is OR.sup.1' or NR.sup.1''R.sup.1''', wherein
R.sup.1' is hydrogen, C.sub.1-C.sub.8 alkyl, or C.sub.7-C.sub.10
arylalkyl, and R.sup.1'' and R.sup.1''' are independently hydrogen,
C.sub.1-C.sub.12 alkyl, C.sub.3-C.sub.12 alkenyl, or
C.sub.3-C.sub.12 alkynyl;
[0218] R.sup.2 is halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
haloalkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, cyano, or a group of the formula
--CR.sup.17.dbd.CR.sup.18--SiR.sup.19R.sup.20R.sup.21, wherein
R.sup.17 is hydrogen, F, or Cl; R.sup.18 is hydrogen, F, Cl,
C.sub.1-C.sub.4 alkyl, or C.sub.1-C.sub.4 haloalkyl; and R.sup.19,
R.sup.20, and R.sup.21 are independently C.sub.1-C.sub.10 alkyl,
C.sub.3-C.sub.6 cycloalkyl, phenyl, substituted phenyl,
C.sub.1-C.sub.10 alkoxy, or OH;
[0219] R.sup.3 and R.sup.4 are independently hydrogen,
C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6
alkenyl, C.sub.3-C.sub.6 haloalkenyl, C.sub.3-C.sub.6 alkynyl,
formyl, C.sub.1-C.sub.3 alkylcarbonyl, C.sub.1-C.sub.3
haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl, C.sub.1-C.sub.6
alkylcarbamyl, C.sub.1-C.sub.6 alkylsulfonyl, C.sub.1-C.sub.6
trialkylsilyl, C.sub.1-C.sub.6 dialkylphosphonyl, or R.sup.3 and
R.sup.4 taken together with N is a 5- or 6-membered saturated ring,
or R.sup.3 and R.sup.4 taken together represent
.dbd.CR.sup.3'(R.sup.4'), wherein R.sup.3' and R.sup.4' are
independently hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.3-C.sub.6
alkenyl, C.sub.3-C.sub.6 alkynyl, C.sub.1-C.sub.6 alkoxy or
C.sub.1-C.sub.6 alkylamino, or, R.sup.3' and R.sup.4' taken
together with .dbd.C represent a 5- or 6-membered saturated
ring;
[0220] A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13,
A14, A15, A16, A17, A18, A19, or A20;
[0221] R.sup.5 is hydrogen, halogen, C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, cyclopropyl, halocyclopropyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3
haloalkoxy, C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, OH, or CN;
[0222] R.sup.6, R.sup.6', and R.sup.6'' are independently
C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, halocyclopropyl,
C.sub.3-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 haloalkoxy,
C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3 haloalkylthio,
C.sub.1-C.sub.4 alkylamino or C.sub.2-C.sub.4 haloalkylamino, or
NO.sub.2;
[0223] R.sup.7 and R.sup.7' are independently hydrogen, halogen,
C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, cyclopropyl,
halocyclopropyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4
haloalkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy,
C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio,
C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino,
C.sub.2-C.sub.4 haloalkylamino, or phenyl; and
[0224] R.sup.8 is hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6
haloalkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 haloalkenyl,
C.sub.3-C.sub.6 alkynyl, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl,
C.sub.1-C.sub.6 alkylcarbamyl, C.sub.1-C.sub.6 alkylsulfonyl,
C.sub.1-C.sub.6 trialkylsilyl, or phenyl.
[0225] In some of these embodiments, R.sup.1 is OR.sup.1. In some
of these embodiments, X is CF. In some of these embodiments, A is
A15. In some of these embodiments, R.sup.5 is F.
[0226] In some embodiments:
[0227] X is N or CY, wherein Y is hydrogen, halogen,
C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 haloalkyl, C.sub.1-C.sub.3
alkoxy, C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio, or
C.sub.1-C.sub.3 haloalkylthio;
[0228] R.sup.1 is OR.sup.1' or NR.sup.1''R.sup.1''', wherein
R.sup.1' is hydrogen, C.sub.1-C.sub.8 alkyl, or C.sub.7-C.sub.10
arylalkyl, and R.sup.1'' and R.sup.1''' are independently hydrogen,
C.sub.1-C.sub.12 alkyl, C.sub.3-C.sub.12 alkenyl, or
C.sub.3-C.sub.12 alkynyl;
[0229] R.sup.2 is halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
haloalkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, cyano, or a group of the formula
--CR.sup.17.dbd.CR.sup.18--SiR.sup.19R.sup.20R.sup.21, wherein
R.sup.17 is hydrogen, F, or Cl; R.sup.18 is hydrogen, F, Cl,
C.sub.1-C.sub.4 alkyl, or C.sub.1-C.sub.4 haloalkyl; and R.sup.19,
R.sup.20, and R.sup.21 are independently C.sub.1-C.sub.10 alkyl,
C.sub.3-C.sub.6 cycloalkyl, phenyl, substituted phenyl,
C.sub.1-C.sub.10 alkoxy, or OH;
[0230] R.sup.3 and R.sup.4 are independently hydrogen,
C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6
alkenyl, C.sub.3-C.sub.6 haloalkenyl, C.sub.3-C.sub.6 alkynyl,
formyl, C.sub.1-C.sub.3 alkylcarbonyl, C.sub.1-C.sub.3
haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl, C.sub.1-C.sub.6
alkylcarbamyl, C.sub.1-C.sub.6 alkylsulfonyl, C.sub.1-C.sub.6
dialkylphosphonyl, or R.sup.3 and R.sup.4 taken together with N is
a 5- or 6-membered saturated ring, or R.sup.3 and R.sup.4 taken
together represent .dbd.CR.sup.3'(R.sup.4'), wherein R.sup.3' and
R.sup.4' are independently hydrogen, C.sub.1-C.sub.6 alkyl,
C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 alkynyl, C.sub.1-C.sub.6
alkoxy or C.sub.1-C.sub.6 alkylamino, or, R.sup.3' and R.sup.4'
taken together with .dbd.C represent a 5- or 6-membered saturated
ring;
[0231] A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13,
A14, A15, A16, A17, or A18;
[0232] R.sup.5 is hydrogen, halogen, C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, cyclopropyl, halocyclopropyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3
haloalkoxy, C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, OH, or CN;
[0233] R.sup.6, R.sup.6', and R.sup.6'' are independently hydrogen,
halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl,
cyclopropyl, halocyclopropyl, C.sub.2-C.sub.4 alkenyl,
C.sub.2-C.sub.4 haloalkenyl, C.sub.2-C.sub.4 alkynyl,
C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3
alkylthio, C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4
alkylamino or C.sub.2-C.sub.4 haloalkylamino, OH, CN, or
NO.sub.2;
[0234] R.sup.7 and R.sup.7' are independently C.sub.1-C.sub.4
alkyl, C.sub.1-C.sub.4 haloalkyl, halocyclopropyl, C.sub.2-C.sub.4
alkenyl, C.sub.2-C.sub.4 haloalkenyl, C.sub.2-C.sub.4 alkynyl,
C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 haloalkylthio, amino,
C.sub.4 alkylamino, or C.sub.2-C.sub.4 haloalkylamino; and
[0235] R.sup.8 is hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6
haloalkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 haloalkenyl,
C.sub.3-C.sub.6 alkynyl, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl,
C.sub.1-C.sub.6 alkylcarbamyl, C.sub.1-C.sub.6 alkylsulfonyl,
C.sub.1-C.sub.6 trialkylsilyl, or phenyl.
[0236] In some of these embodiments, R.sup.1 is OR.sup.1. In some
of these embodiments, X is CF. In some of these embodiments, A is
A15. In some of these embodiments, R.sup.5 is F.
[0237] In some embodiments:
[0238] X is N or CY, wherein Y is hydrogen, halogen,
C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 haloalkyl, C.sub.1-C.sub.3
alkoxy, C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio, or
C.sub.1-C.sub.3 haloalkylthio;
[0239] R.sup.1 is OR.sup.1' or NR.sup.1''R.sup.1''', wherein
R.sup.1' is hydrogen, C.sub.1-C.sub.8 alkyl, or C.sub.7-C.sub.10
arylalkyl, and R.sup.1'' and R.sup.1''' are independently hydrogen,
C.sub.1-C.sub.12 alkyl, C.sub.3-C.sub.12 alkenyl, or
C.sub.3-C.sub.12 alkynyl;
[0240] R.sup.2 is halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
haloalkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, cyano, or a group of the formula
--CR.sup.17.dbd.CR.sup.18--SiR.sup.19R.sup.20R.sup.21, wherein
R.sup.17 is hydrogen, F, or Cl; R.sup.18 is hydrogen, F, Cl,
C.sub.1-C.sub.4 alkyl, or C.sub.1-C.sub.4 haloalkyl; and R.sup.19,
R.sup.20, and R.sup.21 are independently C.sub.1-C.sub.10 alkyl,
C.sub.3-C.sub.6 cycloalkyl, phenyl, substituted phenyl,
C.sub.1-C.sub.10 alkoxy, or OH;
[0241] R.sup.3 and R.sup.4 are independently hydrogen,
C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6
alkenyl, C.sub.3-C.sub.6 haloalkenyl, C.sub.3-C.sub.6 alkynyl,
formyl, C.sub.1-C.sub.3 alkylcarbonyl, C.sub.1-C.sub.3
haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl, C.sub.1-C.sub.6
alkylcarbamyl, C.sub.1-C.sub.6 alkylsulfonyl, C.sub.1-C.sub.6
trialkylsilyl, C.sub.1-C.sub.6 dialkylphosphonyl, or R.sup.3 and
R.sup.4 taken together with N is a 5- or 6-membered saturated ring,
or R.sup.3 and R.sup.4 taken together represent
.dbd.CR.sup.3'(R.sup.4'), wherein R.sup.3' and R.sup.4' are
independently hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.3-C.sub.6
alkenyl, C.sub.3-C.sub.6 alkynyl, C.sub.1-C.sub.6 alkoxy or
C.sub.1-C.sub.6 alkylamino, or, R.sup.3' and R.sup.4' taken
together with .dbd.C represent a 5- or 6-membered saturated
ring;
[0242] A is A3, A6, A11, A12, A15, A18, A19, or A20;
[0243] R.sup.5 is hydrogen, halogen, C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, cyclopropyl, halocyclopropyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3
haloalkoxy, C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, OH, or CN;
[0244] R.sup.6, R.sup.6', and R.sup.6'' are independently hydrogen,
halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl,
cyclopropyl, halocyclopropyl, C.sub.2-C.sub.4 alkenyl,
C.sub.2-C.sub.4 haloalkenyl, C.sub.2-C.sub.4 alkynyl,
C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3
alkylthio, C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4
alkylamino or C.sub.2-C.sub.4 haloalkylamino, OH, CN, or
NO.sub.2;
[0245] R.sup.7 and R.sup.7' are independently hydrogen, halogen,
C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, cyclopropyl,
halocyclopropyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4
haloalkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy,
C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio,
C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino,
C.sub.2-C.sub.4 haloalkylamino, or phenyl; and
[0246] R.sup.8 is C.sub.3-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl,
C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 haloalkenyl,
C.sub.3-C.sub.6 alkynyl, formyl, C.sub.1-C.sub.3 haloalkylcarbonyl,
C.sub.1-C.sub.6 alkoxycarbonyl, C.sub.1-C.sub.6 alkylcarbamyl,
C.sub.1-C.sub.6 alkylsulfonyl, or C.sub.1-C.sub.6
trialkylsilyl.
[0247] In some of these embodiments, R.sup.1 is OR.sup.1. In some
of these embodiments, X is CF. In some of these embodiments, A is
A15. In some of these embodiments, R.sup.5 is F.
[0248] In certain embodiments, the pyridine carboxylic acid
herbicide is a compound defined by Formula (II):
##STR00027##
wherein
[0249] R.sup.1 is OR.sup.1' or NR.sup.1''R.sup.1''', wherein
R.sup.1' is hydrogen, C.sub.1-C.sub.8 alkyl, or C.sub.7-C.sub.10
arylalkyl, and R.sup.1'' and R.sup.1''' are independently hydrogen,
C.sub.1-C.sub.12 alkyl, C.sub.3-C.sub.12 alkenyl, or
C.sub.3-C.sub.12 alkynyl;
[0250] R.sup.2 is halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
haloalkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, cyano, or a group of the formula
--CR.sup.17.dbd.CR.sup.18--SiR.sup.19R.sup.20R.sup.21, wherein
R.sup.17 is hydrogen, F, or Cl; R.sup.18 is hydrogen, F, Cl,
C.sub.1-C.sub.4 alkyl, or C.sub.1-C.sub.4 haloalkyl; and R.sup.19,
R.sup.20, and R.sup.21 are independently C.sub.1-C.sub.10 alkyl,
C.sub.3-C.sub.6 cycloalkyl, phenyl, substituted phenyl,
C.sub.1-C.sub.10 alkoxy, or OH;
[0251] R.sup.3 and R.sup.4 are independently hydrogen,
C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6
alkenyl, C.sub.3-C.sub.6 haloalkenyl, C.sub.3-C.sub.6 alkynyl,
formyl, C.sub.1-C.sub.3 alkylcarbonyl, C.sub.1-C.sub.3
haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl, C.sub.1-C.sub.6
alkylcarbamyl, C.sub.1-C.sub.6 alkylsulfonyl, C.sub.1-C.sub.6
trialkylsilyl, C.sub.1-C.sub.6 dialkylphosphonyl, or R.sup.3 and
R.sup.4 taken together with N is a 5- or 6-membered saturated ring,
or R.sup.3 and R.sup.4 taken together represent
.dbd.CR.sup.3'(R.sup.4'), wherein R.sup.3' and R.sup.4' are
independently hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.3-C.sub.6
alkenyl, C.sub.3-C.sub.6 alkynyl, C.sub.1-C.sub.6 alkoxy or
C.sub.1-C.sub.6 alkylamino, or, R.sup.3' and R.sup.4' taken
together with .dbd.C represent a 5- or 6-membered saturated
ring;
[0252] A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13,
A14, A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26,
A27, A28, A29, A30, A31, A32, A33, A34, A35, or A36;
[0253] R.sup.5 is hydrogen, halogen, C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, cyclopropyl, halocyclopropyl,
C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3
haloalkoxy, C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, OH, or CN;
[0254] R.sup.6, R.sup.6', and R.sup.6'' are independently hydrogen,
halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl,
cyclopropyl, halocyclopropyl, C.sub.2-C.sub.4 alkenyl,
C.sub.2-C.sub.4 haloalkenyl, C.sub.2-C.sub.4 alkynyl,
C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3
alkylthio, C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4
alkylamino or C.sub.2-C.sub.4 haloalkylamino, OH, CN, or
NO.sub.2;
[0255] R.sup.7 and R.sup.7' are independently hydrogen, halogen,
C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, cyclopropyl,
halocyclopropyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4
haloalkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy,
C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio,
C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino,
C.sub.2-C.sub.4 haloalkylamino, or phenyl; and
[0256] R.sup.8 is hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6
haloalkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 haloalkenyl,
C.sub.3-C.sub.6 alkynyl, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl,
C.sub.1-C.sub.6 alkylcarbamyl, C.sub.1-C.sub.6 alkylsulfonyl,
C.sub.1-C.sub.6 trialkylsilyl, or phenyl;
[0257] or an agriculturally acceptable N-oxide or salt thereof.
[0258] In some embodiments:
[0259] R.sup.1 is OR.sup.1', wherein R.sup.1' is hydrogen,
C.sub.1-C.sub.8 alkyl, or C.sub.7-C.sub.10 arylalkyl;
[0260] R.sup.2 is halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
haloalkyl, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, or C.sub.1-C.sub.4
haloalkylthio.
[0261] R.sup.3 and R.sup.4 are hydrogen, C.sub.1-C.sub.6 alkyl,
C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6
haloalkenyl, C.sub.3-C.sub.6 alkynyl, formyl, C.sub.1-C.sub.3
alkylcarbonyl, C.sub.1-C.sub.3 haloalkylcarbonyl, or R.sup.3 and
R.sup.4 taken together represent .dbd.CR.sup.3'(R.sup.4'), wherein
R.sup.3' and R.sup.4' are independently hydrogen, C.sub.1-C.sub.6
alkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 alkynyl,
C.sub.1-C.sub.6 alkoxy or C.sub.1-C.sub.6 alkylamino;
[0262] A is A1, A2, A3, A7, A8, A9, A10, A11, A12, A13, A14, A15,
A21, A22, A23, A24, A27, A28, A29, A30, A31, or A32;
[0263] R.sup.5 is hydrogen, halogen, C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4
haloalkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy,
C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio,
C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino,
or C.sub.2-C.sub.4 haloalkylamino;
[0264] R.sup.6, R.sup.6', and R.sup.6'' are independently hydrogen,
halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl,
cyclopropyl, halocyclopropyl, C.sub.2-C.sub.4 alkenyl,
C.sub.2-C.sub.4 haloalkenyl, C.sub.2-C.sub.4 alkynyl,
C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3 haloalkoxy, CN, or
NO.sub.2;
[0265] R.sup.7 and R.sup.7' are independently hydrogen, halogen,
C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, C.sub.1-C.sub.3
alkoxy, C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio,
cyclopropyl, amino or C.sub.1-C.sub.4 alkylamino; and
[0266] R.sup.8 is hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.4
haloalkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 haloalkenyl,
formyl, C.sub.1-C.sub.3 alkylcarbonyl, C.sub.1-C.sub.3
haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl, or
C.sub.1-C.sub.6 alkylcarbamyl.
[0267] In some embodiments, R.sup.1 is OR.sup.1', wherein R.sup.1'
is hydrogen, C.sub.1-C.sub.8 alkyl, or C.sub.7-C.sub.10
arylalkyl.
[0268] In some embodiments, R.sup.2 is halogen,
C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4 haloalkenyl, or
C.sub.1-C.sub.4-alkoxy. In certain embodiments, R.sup.2 is Cl,
methoxy, vinyl, or 1-propenyl. In some embodiments, R.sup.3 and
R.sup.4 are hydrogen.
[0269] In some embodiments, A is A1, A2, A3, A7, A8, A9, A10, A13,
A14, or A15. In certain embodiments, A is A1, A2, A3, A13, A14, or
A15. In certain embodiments, A is A15.
[0270] In some embodiments, R.sup.5 is hydrogen or F. In certain
embodiments, R.sup.5 is F. In certain embodiments, R.sup.5 is
H.
[0271] In some embodiments, R.sup.6 is hydrogen or F. In certain
embodiments, R.sup.6 is F. In certain embodiments, R.sup.6 is H. In
some embodiments, R.sup.6'' is hydrogen, halogen, C.sub.1-C.sub.4
alkyl, C.sub.1-C.sub.4 haloalkyl, cyclopropyl, C.sub.2-C.sub.4
alkynyl, CN, or NO.sub.2. In certain embodiments, R.sup.6,
R.sup.6', and R.sup.6'' are all hydrogen.
[0272] In certain embodiments, R.sup.2 is Cl, methoxy, vinyl, or
1-propenyl; R.sup.3 and R.sup.4 are hydrogen; A is A15; R.sup.5 is
hydrogen or F; R.sup.6 is hydrogen or F; and R.sup.6'' is hydrogen,
halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl,
cyclopropyl, C.sub.2-C.sub.4 alkynyl, CN, or NO.sub.2.
[0273] In certain embodiments, the pyridine carboxylic acid
herbicide is a compound defined by Formula (III):
##STR00028##
wherein
[0274] X is N or CY, wherein Y is hydrogen, halogen,
C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 haloalkyl, C.sub.1-C.sub.3
alkoxy, C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio or
C.sub.1-C.sub.3 haloalkylthio;
[0275] R.sup.1 is OR.sup.1' or NR.sup.1''R.sup.1''', wherein
R.sup.1' is hydrogen, C.sub.1-C.sub.8 alkyl, or C.sub.7-C.sub.10
arylalkyl, and R.sup.1'' and R.sup.1''' are independently hydrogen,
C.sub.1-C.sub.12 alkyl, C.sub.3-C.sub.12 alkenyl, or
C.sub.3-C.sub.12 alkynyl;
[0276] R.sup.2 is halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
haloalkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, C.sub.1-C.sub.4
haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino, C.sub.2-C.sub.4
haloalkylamino, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, cyano, or a group of the formula
--CR.sup.17.dbd.CR.sup.18--SiR.sup.19R.sup.20R.sup.21, wherein
R.sup.17 is hydrogen, F, or Cl; R.sup.18 is hydrogen, F, Cl,
C.sub.1-C.sub.4 alkyl, or C.sub.1-C.sub.4 haloalkyl; and R.sup.19,
R.sup.20, and R.sup.21 are independently C.sub.1-C.sub.10 alkyl,
C.sub.3-C.sub.6 cycloalkyl, phenyl, substituted phenyl,
C.sub.1-C.sub.10 alkoxy, or OH;
[0277] R.sup.3 and R.sup.4 are independently hydrogen,
C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6
alkenyl, C.sub.3-C.sub.6 haloalkenyl, C.sub.3-C.sub.6 alkynyl,
formyl, C.sub.1-C.sub.3 alkylcarbonyl, C.sub.1-C.sub.3
haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl, C.sub.1-C.sub.6
alkylcarbamyl, C.sub.1-C.sub.6 alkylsulfonyl, C.sub.1-C.sub.6
trialkylsilyl, C.sub.1-C.sub.6 dialkylphosphonyl, or R.sup.3 and
R.sup.4 taken together with N is a 5- or 6-membered saturated ring,
or R.sup.3 and R.sup.4 taken together represent
.dbd.CR.sup.3'(R.sup.4'), wherein R.sup.3' and R.sup.4' are
independently hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.3-C.sub.6
alkenyl, C.sub.3-C.sub.6 alkynyl, C.sub.1-C.sub.6 alkoxy or
C.sub.1-C.sub.6 alkylamino, or, R.sup.3' and R.sup.4' taken
together with .dbd.C represent a 5- or 6-membered saturated
ring;
[0278] R.sup.6 and R.sup.6' are independently hydrogen, halogen,
C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, cyclopropyl,
halocyclopropyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4
haloalkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy,
C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio,
C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino or
C.sub.2-C.sub.4 haloalkylamino, OH, CN, or NO.sub.2;
[0279] R.sup.7 and R.sup.7' are independently hydrogen, halogen,
C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, cyclopropyl,
halocyclopropyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4
haloalkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy,
C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio,
C.sub.1-C.sub.3 haloalkylthio, amino, C.sub.1-C.sub.4 alkylamino,
C.sub.2-C.sub.4 haloalkylamino, or phenyl; and
[0280] R.sup.8 is hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6
haloalkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 haloalkenyl,
C.sub.3-C.sub.6 alkynyl, formyl, C.sub.1-C.sub.3 alkylcarbonyl,
C.sub.1-C.sub.3 haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl,
C.sub.1-C.sub.6 alkylcarbamyl, C.sub.1-C.sub.6 alkylsulfonyl,
C.sub.1-C.sub.6 trialkylsilyl, or phenyl;
or an agriculturally acceptable N-oxide or salt thereof.
[0281] In some embodiments:
[0282] X is N, CH, CF, CCl, or CBr;
[0283] R.sup.1 is OR.sup.1', wherein is hydrogen, C.sub.1-C.sub.8
alkyl, or C.sub.7-C.sub.10 arylalkyl;
[0284] R.sup.2 is halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
haloalkyl, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4 haloalkenyl,
C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4
haloalkoxy, C.sub.1-C.sub.4 alkylthio, or C.sub.1-C.sub.4
haloalkylthio;
[0285] R.sup.3 and R.sup.4 are hydrogen, C.sub.1-C.sub.6 alkyl,
C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6
haloalkenyl, C.sub.3-C.sub.6 alkynyl, formyl, C.sub.1-C.sub.3
alkylcarbonyl, C.sub.1-C.sub.3 haloalkylcarbonyl, or R.sup.3 and
R.sup.4 taken together represent .dbd.CR.sup.3'(R.sup.4'), wherein
R.sup.3' and R.sup.4' are independently hydrogen, C.sub.1-C.sub.6
alkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 alkynyl,
C.sub.1-C.sub.6 alkoxy or C.sub.1-C.sub.6 alkylamino;
[0286] R.sup.6 and R.sup.6' are independently hydrogen, halogen,
C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, cyclopropyl,
halocyclopropyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4
haloalkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.3 alkoxy,
C.sub.1-C.sub.3 haloalkoxy, CN, or NO.sub.2;
[0287] R.sup.7 and R.sup.7' are independently hydrogen, halogen,
C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, C.sub.1-C.sub.3
alkoxy, C.sub.1-C.sub.3 haloalkoxy, C.sub.1-C.sub.3 alkylthio,
cyclopropyl, amino or C.sub.1-C.sub.4 alkylamino; and
[0288] R.sup.8 is hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.4
haloalkyl, C.sub.3-C.sub.6 alkenyl, C.sub.3-C.sub.6 haloalkenyl,
formyl, C.sub.1-C.sub.3 alkylcarbonyl, C.sub.1-C.sub.3
haloalkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl, or
C.sub.1-C.sub.6 alkylcarbamyl.
[0289] In some embodiments, X is N, CH or CF. In some embodiments,
X is N. In some embodiments, X is CH. In some embodiments, X is CF.
In other embodiments, X is C--CH.sub.3.
[0290] In some embodiments, R.sup.2 is halogen,
C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4 haloalkenyl, or
C.sub.1-C.sub.4-alkoxy. In certain embodiments, R.sup.2 is Cl,
methoxy, vinyl, or 1-propenyl. In some embodiments, R.sup.3 and
R.sup.4 are hydrogen.
[0291] In some embodiments, R.sup.6 is hydrogen or F. In certain
embodiments, R.sup.6 is F. In certain embodiments, R.sup.6 is H. In
some embodiments, R.sup.6' is hydrogen, halogen, C.sub.1-C.sub.4
alkyl, C.sub.1-C.sub.4 haloalkyl, cyclopropyl, C.sub.2-C.sub.4
alkynyl, CN, or NO.sub.2. In certain embodiments, R.sup.6 and
R.sup.6' are both hydrogen.
[0292] In certain embodiments, R.sup.7 and R.sup.7' are both
hydrogen.
[0293] In certain embodiments, R.sup.6, R.sup.6', R.sup.7, and
R.sup.7' are all hydrogen.
[0294] In certain embodiments, X is CF, R.sup.1 is OR.sup.1',
wherein R.sup.1' is hydrogen, C.sub.1-C.sub.8 alkyl, or
C.sub.7-C.sub.10 arylalkyl; R.sup.2 is Cl, methoxy, vinyl, or
1-propenyl; R.sup.3 and R.sup.4 are hydrogen; R.sup.6 is hydrogen
or F; and R.sup.6' is hydrogen, halogen, C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 haloalkyl, cyclopropyl, C.sub.2-C.sub.4 alkynyl,
CN, or NO.sub.2.
[0295] In certain embodiments, the pyridine carboxylic acid
herbicide is one of Compounds 1-7, the structures of which are
shown in the table below.
TABLE-US-00001 Compound No. Structure 1 ##STR00029## 2 ##STR00030##
3 ##STR00031## 4 ##STR00032## 5 ##STR00033## 6 ##STR00034## 7
##STR00035##
[0296] In certain embodiments, the pyridine carboxylic acid
herbicide is 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)
picolinic acid or an agriculturally acceptable N-oxide, salt, or
ester thereof.
[0297] In some embodiments, the pyridine carboxylic acid herbicide
can be provided as an agriculturally acceptable salt. Exemplary
agriculturally acceptable salts of the pyridine carboxylic acid
herbicides include, but are not limited to, sodium salts, potassium
salts, ammonium salts or substituted ammonium salts, in particular
mono-, di- and tri-C.sub.1-C.sub.8 alkylammonium salts such as
methyl ammonium, dimethylammonium and isopropylammonium, mono-, di-
and tri-hydroxy-C.sub.2-C.sub.8-alkylammonium salts such as
hydroxyethylammonium, di(hydroxyethyl)ammonium,
tri(hydroxyethyl)ammonium, hydroxypropylammonium,
di(hydroxypropyl)ammonium and tri(hydroxypropyl)ammonium salts,
olamine salts, diglycolamine salts, choline salts, and quaternary
ammonium salts such as those represented by the formula
R.sup.9R.sup.10R.sup.11R.sup.12N.sup.+ and wherein R.sup.9,
R.sup.10, R.sup.11 and R.sup.12 (e.g., R.sup.9-R.sup.12) each
independently can represent hydrogen, C.sub.1-C.sub.10 alkyl,
C.sub.2-C.sub.8 alkenyl, C.sub.2-C.sub.8 alkynyl, C.sub.1-C.sub.8
alkoxy, C.sub.1-C.sub.8 alkylthio, or aryl groups, provided that
R.sup.9-R.sup.12 are sterically compatible.
[0298] In some embodiments, the pyridine carboxylic acid herbicide
can be provided as an agriculturally acceptable ester. Suitable
esters include, but are not limited to, C.sub.1-C.sub.8-alkyl
esters and C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub.4-alkyl esters,
such as methyl esters, ethyl esters, isopropyl, butyl, hexyl,
heptyl, isoheptyl, isooctyl, 2-ethylhexyl, butoxyethyl esters,
substituted or unsubstituted aryl esters, orthoesters, and
substituted or unsubstituted arylalkyl esters. In some embodiments,
the ester is a C.sub.1-C.sub.8 alkyl ester, wherein the
C.sub.1-C.sub.8 alkyl group is optionally substituted with one or
more moieties selected from the group of cyano, C.sub.2-C.sub.8
alkoxy, and C.sub.2-C.sub.8 alkylsulfonyl. For example, the ester
is a methyl, --CH.sub.2CN, --CH.sub.2OCH.sub.3,
--CH.sub.2OCH.sub.2CH.sub.2OCH.sub.3, or
--CH.sub.2CH.sub.2SO.sub.2CH.sub.3 ester.
[0299] In some embodiments, the ester is a substituted or
unsubstituted benzyl ester. In some embodiments, the ester is a
benzyl ester optionally substituted with one or more moieties
selected from the group of halogen, C.sub.1-C.sub.2 alkyl,
C.sub.1-C.sub.2 haloalkyl, and combinations thereof. In some
embodiments, the ester is a methyl ester.
[0300] The pyridine carboxylic acid herbicide, or an agriculturally
acceptable N-oxide, salt, or ester thereof, can be applied to
vegetation or an area adjacent the vegetation or applied to soil or
water to prevent the emergence or growth of vegetation in an amount
sufficient to induce a herbicidal effect. In some embodiments, the
pyridine carboxylic acid herbicide, or an agriculturally acceptable
N-oxide, salt, or ester thereof, is applied to vegetation or an
area adjacent the vegetation or applied to soil or water to prevent
the emergence or growth of vegetation in an amount of 0.5 grams
acid equivalent per hectare (g ae/ha) or greater (e.g., 0.6 g ae/ha
or greater, 0.7 g ae/ha or greater, 0.8 g ae/ha or greater, 0.9 g
ae/ha or greater, 1 g ae/ha or greater, 1.1 g ae/ha or greater, 1.2
g ae/ha or greater, 1.3 g ae/ha or greater, 1.4 g ae/ha or greater,
1.5 g ae/ha or greater, 1.6 g ae/ha or greater, 1.7 g ae/ha or
greater, 1.8 g ae/ha or greater, 1.9 g ae/ha or greater, 2 g ae/ha
or greater, 2.25 g ae/ha or greater, 2.5 g ae/ha or greater, 2.75 g
ae/ha or greater, 3 g ae/ha or greater, 4 g ae/ha or greater, 5 g
ae/ha or greater, 6 g ae/ha or greater, 7 g ae/ha or greater, 8 g
ae/ha or greater, 9 g ae/ha or greater, 10 g ae/ha or greater, 11 g
ae/ha or greater, 12 g ae/ha or greater, 13 g ae/ha or greater, 14
g ae/ha or greater, 15 g ae/ha or greater, 16 g ae/ha or greater,
17 g ae/ha or greater, 18 g ae/ha or greater, 19 g ae/ha or
greater, 20 g ae/ha or greater, 21 g ae/ha or greater, 22 g ae/ha
or greater, 23 g ae/ha or greater, 24 g ae/ha or greater, 25 g
ae/ha or greater, 26 g ae/ha or greater, 27 g ae/ha or greater, 28
g ae/ha or greater, 29 g ae/ha or greater, 30 g ae/ha or greater,
31 g ae/ha or greater, 32 g ae/ha or greater, 33 g ae/ha or
greater, 34 g ae/ha or greater, 35 g ae/ha or greater, 36 g ae/ha
or greater, 37 g ae/ha or greater, 38 g ae/ha or greater, 39 g
ae/ha or greater, 40 g ae/ha or greater, 41 g ae/ha or greater, 42
g ae/ha or greater, 43 g ae/ha or greater, 44 g ae/ha or greater,
45 g ae/ha or greater, 46 g ae/ha or greater, 47 g ae/ha or
greater, 48 g ae/ha or greater, 49 g ae/ha or greater, 50 g ae/ha
or greater, 55 g ae/ha or greater, 60 g ae/ha or greater, 65 g
ae/ha or greater, 70 g ae/ha or greater, 75 g ae/ha or greater, 80
g ae/ha or greater, 85 g ae/ha or greater, 90 g ae/ha or greater,
95 g ae/ha or greater, 100 g ae/ha or greater, 110 g ae/ha or
greater, 120 g ae/ha or greater, 130 g ae/ha or greater, 140 g
ae/ha or greater, 150 g ae/ha or greater, 160 g ae/ha or greater,
170 g ae/ha or greater, 180 g ae/ha or greater, 190 g ae/ha or
greater, 200 g ae/ha or greater, 210 g ae/ha or greater, 220 g
ae/ha or greater, 230 g ae/ha or greater, 240 g ae/ha or greater,
250 g ae/ha or greater, 260 g ae/ha or greater, 270 g ae/ha or
greater, 280 g ae/ha or greater, or 290 g ae/ha or greater).
[0301] In some embodiments, the pyridine carboxylic acid herbicide,
or an agriculturally acceptable N-oxide, salt, or ester thereof, is
applied to vegetation or an area adjacent the vegetation or applied
to soil or water to prevent the emergence or growth of vegetation
in an amount of 300 g ae/ha or less (e.g., 290 g ae/ha or less, 280
g ae/ha or less, 270 g ae/ha or less, 260 g ae/ha or less, 250 g
ae/ha or less, 240 g ae/ha or less, 230 g ae/ha or less, 220 g
ae/ha or less, 210 g ae/ha or less, 200 g ae/ha or less, 190 g
ae/ha or less, 180 g ae/ha or less, 170 g ae/ha or less, 160 g
ae/ha or less, 150 g ae/ha or less, 140 g ae/ha or less, 130 g
ae/ha or less, 120 g ae/ha or less, 110 g ae/ha or less, 100 g
ae/ha or less, 95 g ae/ha or less, 90 g ae/ha or less, 85 g ae/ha
or less, 80 g ae/ha or less, 75 g ae/ha or less, 70 g ae/ha or
less, 65 g ae/ha or less, 60 g ae/ha or less, 55 g ae/ha or less,
50 g ae/ha or less, 49 g ae/ha or less, 48 g ae/ha or less, 47 g
ae/ha or less, 46 g ae/ha or less, 45 g ae/ha or less, 44 g ae/ha
or less, 43 g ae/ha or less, 42 g ae/ha or less, 41 g ae/ha or
less, 40 g ae/ha or less, 39 g ae/ha or less, 38 g ae/ha or less,
37 g ae/ha or less, 36 g ae/ha or less, 35 g ae/ha or less, 34 g
ae/ha or less, 33 g ae/ha or less, 32 g ae/ha or less, 31 g ae/ha
or less, 30 g ae/ha or less, 29 g ae/ha or less, 28 g ae/ha or
less, 27 g ae/ha or less, 26 g ae/ha or less, 25 g ae/ha or less,
24 g ae/ha or less, 23 g ae/ha or less, 22 g ae/ha or less, 21 g
ae/ha or less, 20 g ae/ha or less, 19 g ae/ha or less, 18 g ae/ha
or less, 17 g ae/ha or less, 16 g ae/ha or less, 15 g ae/ha or
less, 14 g ae/ha or less, 13 g ae/ha or less, 12 g ae/ha or less,
11 g ae/ha or less, 10 g ae/ha or less, 9 g ae/ha or less, 8 g
ae/ha or less, 7 g ae/ha or less, 6 g ae/ha or less, 5 g ae/ha or
less, 4 g ae/ha or less, 3 g ae/ha or less, 2.75 g ae/ha or less,
2.5 g ae/ha or less, 2.25 g ae/ha or less, 2 g ae/ha or less, 1.9 g
ae/ha or less, 1.8 g ae/ha or less, 1.7 g ae/ha or less, 1.6 g
ae/ha or less, 1.5 g ae/ha or less, 1.4 g ae/ha or less, 1.3 g
ae/ha or less, 1.2 g ae/ha or less, 1.1 g ae/ha or less, 1 g ae/ha
or less, 0.9 g ae/ha or less, 0.8 g ae/ha or less, 0.7 g ae/ha or
less, or 0.6 g ae/ha or less).
[0302] The pyridine carboxylic acid herbicide or an agriculturally
acceptable N-oxide, salt, or ester thereof can be applied to
vegetation or an area adjacent the vegetation or applied to soil or
water to prevent the emergence or growth of vegetation in an amount
ranging from any of the minimum values described above to any of
the maximum values described above. In some embodiments, the
pyridine carboxylic acid herbicide, or an agriculturally acceptable
N-oxide, salt, or ester thereof, is applied to vegetation or an
area adjacent the vegetation or applied to soil or water to prevent
the emergence or growth of vegetation in an amount of from 0.5-300
g ae/ha (e.g., from 0.5-5 g ae/ha, from 2.5-40 g ae/ha, from 0.5-40
g ae/ha, from 0.5-2.5 g ae/ha, from 2-150 g ae/ha, from 5-75 g
ae/ha, from 5-40 g ae/ha, from 30-40 g ae/ha, or from 5-15 g
ae/ha). In some embodiments, the pyridine carboxylic acid
herbicide, or an agriculturally acceptable N-oxide, salt, or ester
thereof, is applied in an amount from 30-40 g ae/ha. In some
embodiments, the pyridine carboxylic acid herbicide, or an
agriculturally acceptable N-oxide, salt, or ester thereof, is
applied in an amount from 5-40 g ae/ha.
[0303] HPPD Inhibitors
[0304] In addition to the pyridine carboxylic acid herbicide or
agriculturally acceptable N-oxide, salt or ester thereof, the
compositions can include an inhibitor of 4-hydroxyphenylpyruvate
dioxygenase (HPPD), an oxygenase enzyme involved in the creation of
energy in plants and higher order eukaryotes. Examples of HPPD
inhibitors include benzobicyclon, benzofenap, bicyclopyrone,
fenquinotrione, isoxachlortole, isoxaflutole, mesotrione,
pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tembotrione,
tefuryltrione, topramezone, or an agriculturally acceptable salt
thereof, and combinations thereof.
[0305] The HPPD inhibitor or agriculturally acceptable salt thereof
can be applied to vegetation or an area adjacent to the vegetation
or applied to soil or water to prevent the emergence or growth of
vegetation in an amount sufficient to induce a herbicidal effect.
In some embodiments, the HPPD inhibitor or agriculturally
acceptable salt thereof is applied to vegetation or an area
adjacent the vegetation or applied to soil or water to prevent the
emergence or growth of vegetation in an amount of 1 grams active
ingredient per hectare (g ai/ha) or more (e.g., 2 g ai/ha or more,
4 g ai/ha or more, 6 g ai/ha or more, 8 g ai/ha or more, 10 g ai/ha
or more, 15 g ai/ha or more, 20 g ai/ha or more, 25 g ai/ha or
more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more,
45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g
ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha
or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or
more, 95 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more,
120 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150
g ai/ha or more, 160 g ai/ha or more, 170 g ai/ha or more, 180 g
ai/ha or more, 190 g ai/ha or more, 200 g ai/ha or more, 210 g
ai/ha or more, 220 g ai/ha or more, 230 g ai/ha or more, 240 g
ai/ha or more, 250 g ai/ha or more, 260 g ai/ha or more, 270 g
ai/ha or more, 280 g ai/ha or more, 290 g ai/ha or more, 300 g
ai/ha or more, 310 g ai/ha or more, 320 g ai/ha or more, 330 g
ai/ha or more, 340 g ai/ha or more, 350 g ai/ha or more, 360 g
ai/ha or more, 370 g ai/ha or more, 380 g ai/ha or more, 390 g
ai/ha or more, 400 g ai/ha or more, 420 g ai/ha or more, 440 g
ai/ha or more, 460 g ai/ha or more, 480 g ai/ha or more, 500 g
ai/ha or more, 520 g ai/ha or more, 540 g ai/ha or more, 560 g
ai/ha or more, 580 g ai/ha or more, 600 g ai/ha or more, 625 g
ai/ha or more, 650 g ai/ha or more, 675 g ai/ha or more, 700 g
ai/ha or more, 725 g ai/ha or more, 750 g ai/ha or more, 775 g
ai/ha or more, 800 g ai/ha or more, 825 g ai/ha or more, 850 g
ai/ha or more, 875 g ai/ha or more, 900 g ai/ha or more, 925 g
ai/ha or more, 950 g ai/ha or more, 975 g ai/ha or more, 1000 g
ai/ha or more, 1050 g ai/ha or more, 1100 g ai/ha or more, 1150 g
ai/ha or more, 1200 g ai/ha or more, 1250 g ai/ha or more, 1300 g
ai/ha or more, 1350 g ai/ha or more, 1400 g ai/ha or more, 1450 g
ai/ha or more, 1500 g ai/ha or more, 1550 g ai/ha or more, 1600 g
ai/ha or more, 1650 g ai/ha or more, 1660 g ai/ha or more, 1670 g
ai/ha or more, 1680 g ai/ha or more, 1690 g ai/ha or more, 1700 g
ai/ha or more, 1750 g ai/ha or more, 1800 g ai/ha or more, 1850 g
ai/ha or more, 1900 g ai/ha or more, 1950 g ai/ha or more, 2000 g
ai/ha or more, 2500 g ai/ha or more, 3000 g ai/ha or more, 3500 g
ai/ha or more, 4000 g ai/ha or more, or 4500 g ai/ha or more).
[0306] In some embodiments, the HPPD inhibitor or agriculturally
acceptable salt or ester thereof is applied to vegetation or an
area adjacent the vegetation or applied to soil or water to prevent
the emergence or growth of vegetation in an amount of 4500 g ai/ha
or less (e.g., 4000 g ai/ha or less, 3500 g ai/ha or less, 3000 g
ai/ha or less, 2500 g ai/ha or less, 2000 g ai/ha or less, 1950 g
ai/ha or less, 1900 g ai/ha or less, 1850 g ai/ha or less, 1800 g
ai/ha or less, 1750 g ai/ha or less, 1700 g ai/ha or less, 1690 g
ai/ha or less, 1680 g ai/ha or less, 1670 g ai/ha or less, 1660 g
ai/ha or less, 1650 g ai/ha or less, 1600 g ai/ha or less, 1550 g
ai/ha or less, 1500 g ai/ha or less, 1450 g ai/ha or less, 1400 g
ai/ha or less, 1350 g ai/ha or less, 1300 g ai/ha or less, 1250 g
ai/ha or less, 1200 g ai/ha or less, 1150 g ai/ha or less, 1100 g
ai/ha or less, 1050 g ai/ha or less, 1000 g ai/ha or less, 975 g
ai/ha or less, 950 g ai/ha or less, 925 g ai/ha or less, 900 g
ai/ha or less, 875 g ai/ha or less, 850 g ai/ha or less, 825 g
ai/ha or less, 800 g ai/ha or less, 775 g ai/ha or less, 750 g
ai/ha or less, 725 g ai/ha or less, 700 g ai/ha or less, 675 g
ai/ha or less, 650 g ai/ha or less, 625 g ai/ha or less, 600 g
ai/ha or less, 580 g ai/ha or less, 560 g ai/ha or less, 540 g
ai/ha or less, 520 g ai/ha or less, 500 g ai/ha or less, 480 g
ai/ha or less, 460 g ai/ha or less, 440 g ai/ha or less, 420 g
ai/ha or less, 400 g ai/ha or less, 390 g ai/ha or less, 380 g
ai/ha or less, 370 g ai/ha or less, 360 g ai/ha or less, 350 g
ai/ha or less, 340 g ai/ha or less, 330 g ai/ha or less, 320 g
ai/ha or less, 310 g ai/ha or less, 300 g ai/ha or less, 290 g
ai/ha or less, 280 g ai/ha or less, 270 g ai/ha or less, 260 g
ai/ha or less, 250 g ai/ha or less, 240 g ai/ha or less, 230 g
ai/ha or less, 220 g ai/ha or less, 210 g ai/ha or less, 200 g
ai/ha or less, 190 g ai/ha or less, 180 g ai/ha or less, 170 g
ai/ha or less, 160 g ai/ha or less, 150 g ai/ha or less, 140 g
ai/ha or less, 130 g ai/ha or less, 120 g ai/ha or less, 110 g
ai/ha or less, 100 g ai/ha or less, 95 g ai/ha or less, 90 g ai/ha
or less, 85 g ai/ha or less, 80 g ai/ha or less, 75 g ai/ha or
less, 70 g ai/ha or less, 65 g ai/ha or less, 60 g ai/ha or less,
55 g ai/ha or less, 50 g ai/ha or less, 45 g ai/ha or less, 40 g
ai/ha or less, 35 g ai/ha or less, 30 g ai/ha or less, 25 g ai/ha
or less, 20 g ai/ha or less, 15 g ai/ha or less, 10 g ai/ha or
less, 9 g ai/ha or less, 8 g ai/ha or less, 7 g ai/ha or less, 6 g
ai/ha or less, 5 g ai/ha or less, 4.5 g ai/ha or less, 4 g ai/ha or
less, 3.5 g ai/ha or less, 3 g ai/ha or less, 2.5 g ai/ha or less,
2 g ai/ha or less, 1.5 g ai/ha or less, or 1 g ai/ha or less).
[0307] The HPPD inhibitor or an agriculturally acceptable salt
thereof can be applied to vegetation or an area adjacent the
vegetation or applied to soil or water to prevent the emergence or
growth of vegetation in an amount ranging from any of the minimum
values described above to any of the maximum values described
above. In some embodiments, the HPPD inhibitor or agriculturally
acceptable salt or ester thereof is applied to vegetation or an
area adjacent the vegetation or applied to soil or water to prevent
the emergence or growth of vegetation in an amount of 1-4500 g
ai/ha (e.g., 1-4000 g ai/ha, 1-3000 g ai/ha, 1-2000 g ai/ha, 1-1000
g ai/ha, 1-500 g ai/ha, 1-250 g ai/ha, 1-200 g ai/ha, 1-100 g
ai/ha, 1-50 g ai/ha, 5-45 g ai/ha, 10-40 g ai/ha, 15-35 g ai/ha,
25-1000 g ai/ha, 25-500 g ai/ha, 25-400 g ai/ha, 25-300 g ai/ha,
25-200 g ai/ha, 50-200 g ai/ha, 50-250 g ai/ha, 50-300 g ai/ha,
50-350 g ai/ha, 70-250 g ai/ha, 70-230 g ai/ha, 70-210 g ai/ha,
70-190 g ai/ha, 70-170 g ai/ha, 70-150 g ai/ha, 70-130 g ai/ha,
70-110 g ai/ha, 100-150 g ai/ha, 100-170 g ai/ha, 100-190 g ai/ha,
150-250 g ai/ha, 175-300 g ai/ha, 200-300 g ai/ha, 200-350 g ai/ha,
200-400 g ai/ha, 200-450 g ai/ha, 200-500 g ai/ha, 300-500 g ai/ha,
300-600 g ai/ha, 350-700 g ai/ha, 400-800 g ai/ha, 450-900 g ai/ha,
500-900 g ai/ha, 550-900 g ai/ha, 600-900 g ai/ha, or 650-1000 g
ai/ha).
[0308] In certain embodiments, the herbicidal composition contains
a herbicidally effective amount of (a) a pyridine carboxylic acid
herbicide or an agriculturally acceptable N-oxide, salt, or ester
thereof, and (b) benzobicyclon, benzofenap, bicyclopyrone,
fenquinotrione, isoxachlortole, isoxaflutole, mesotrione,
pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tembotrione,
tefuryltrione, topramezone, or agriculturally acceptable salts, or
combinations thereof
[0309] Benzobicyclon
[0310] Compositions and methods of the present disclosure can
include benzobicyclon or an agriculturally acceptable salt thereof.
Benzobicyclon, shown below, is
3-[2-chloro-4-(methylsulfonyl)benzoyl]-4-(phenylthio)bicyclo[3.2.1]oct-3--
en-2-one. Its herbicidal activity is exemplified in Tomlin, C. D.
S., Ed. The Pesticide Manual: A World Compendium, 15.sup.th ed.;
BCPC: Alton, 2009 (hereafter "The Pesticide Manual, Fifteenth
Edition, 2009"). Exemplary uses of benzobicyclon include its use
for control of annual and perennial paddy weeds in direct-seeded
and transplanted rice, applied early pre- to early post-emergence,
at 0.2-0.3 kilograms per hectare (kg/ha).
##STR00036##
[0311] The benzobicyclon can be applied to vegetation or an area
adjacent to the vegetation or applied to soil or water to prevent
the emergence or growth of vegetation in an amount sufficient to
induce a herbicidal effect. In some embodiments, the benzobicyclon
is applied to vegetation or an area adjacent to the vegetation or
applied to soil or water to prevent the emergence or growth of
vegetation in an amount of 50 g ai/ha or more (e.g., 55 g ai/ha or
more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more,
75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g
ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g
ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g
ai/ha or more, 160 g ai/ha or more, 170 g ai/ha or more, 180 g
ai/ha or more, 190 g ai/ha or more, 200 g ai/ha or more, 220 g
ai/ha or more, 240 g ai/ha or more, 260 g ai/ha or more, 280 g
ai/ha or more, 300 g ai/ha or more, 320 g ai/ha or more, 340 g
ai/ha or more, 360 g ai/ha or more, 380 g ai/ha or more, or 400 g
ai/ha or more).
[0312] In some embodiments, the benzobicyclon or agriculturally
acceptable salt thereof is applied to vegetation or an area
adjacent the vegetation or applied to soil or water to prevent the
emergence or growth of vegetation in an amount of 401 g ai/ha or
less (e.g., 400 g ai/ha or less, 380 g ai/ha or less, 360 g ai/ha
or less, 340 g ai/ha or less, 320 g ai/ha or less, 300 g ai/ha or
less, 280 g ai/ha or less, 260 g ai/ha or less, 240 g ai/ha or
less, 220 g ai/ha or less, 200 g ai/ha or less, 190 g ai/ha or
less, 180 g ai/ha or less, 170 g ai/ha or less, 160 g ai/ha or
less, 150 g ai/ha or less, 140 g ai/ha or less, 130 g ai/ha or
less, 120 g ai/ha or less, 110 g ai/ha or less, 100 g ai/ha or
less, 90 g ai/ha or less, 85 g ai/ha or less, 80 g ai/ha or less,
75 g ai/ha or less, 70 g ai/ha or less, 65 g ai/ha or less, 60 g
ai/ha or less, 55 g ai/ha or less, or 50 g ai/ha or less).
[0313] The benzobicyclon can be applied to vegetation or an area
adjacent to the vegetation or applied to soil or water to prevent
the emergence or growth of vegetation in an amount ranging from any
of the minimum values described above to any of the maximum values
described above. In some embodiments, the benzobicyclon is applied
to vegetation or an area adjacent to the vegetation or applied to
soil or water to prevent the emergence or growth of vegetation in
an amount of 50-400 g ai/ha (e.g., 75-400 g ai/ha, 100-400 g ai/ha,
150-400 g ai/ha, 175-400 g ai/ha, 175-350 g ai/ha, 175-325 g ai/ha,
175-300 g ai/ha, or 200-300 g ai/ha).
[0314] Benzofenap
[0315] Compositions and methods of the present disclosure can
include benzofenap or an agriculturally acceptable salt thereof.
Benzofenap, as well as methods of preparing benzofenap, are known
in the art. Benzofenap, shown below, is
2-[[4-(2,4-dichloro-3-methylbenzoyl)-1,3-dimethyl-1H-pyrazol-5-yl]oxy]-1--
(4-methylphenyl)ethanone. Its herbicidal activity is exemplified in
Tomlin, C. D. S., Ed. The Pesticide Manual: A World Compendium,
15.sup.th ed.; BCPC: Alton, 2009 (hereafter "The Pesticide Manual,
Fifteenth Edition, 2009"). Exemplary uses of benzofenap include its
use for control of broadleaf weeds in rice, applied at 0.6-0.9
kg/ha.
##STR00037##
[0316] The benzofenap or agriculturally acceptable salt thereof can
be applied to vegetation or an area adjacent the vegetation or
applied to soil or water to prevent the emergence or growth of
vegetation in an amount sufficient to induce a herbicidal effect.
In some embodiments, the benzofenap or an agriculturally acceptable
salt thereof is applied to vegetation or an area adjacent the
vegetation or applied to soil or water to prevent the emergence or
growth of vegetation in an amount of of 299 g ai/ha or more (e.g.,
300 g ai/ha or more, 320 g ai/ha or more, 340 g ai/ha or more, 360
g ai/ha or more, 380 g ai/ha or more, 400 g ai/ha or more, 450 g
ai/ha or more, 500 g ai/ha or more, 550 g ai/ha or more, 600 g
ai/ha or more, 625 g ai/ha or more, 650 g ai/ha or more, 675 g
ai/ha or more, 700 g ai/ha or more, 725 g ai/ha or more, 750 g
ai/ha or more, 775 g ai/ha or more, 800 g ai/ha or more, 825 g
ai/ha or more, 850 g ai/ha or more, 875 g ai/ha or more, 900 g
ai/ha or more, 925 g ai/ha or more, 950 g ai/ha or more, 975 g
ai/ha or more, or 1000 g ai/ha or more).
[0317] In some embodiments, the benzofenap is applied to vegetation
or an area adjacent the vegetation or applied to soil or water to
prevent the emergence or growth of vegetation in an amount of of
1001 g ai/ha or less (e.g., 1000 g ai/ha or less, 975 g ai/ha or
less, 950 g ai/ha or less, 925 g ai/ha or less, 900 g ai/ha or
less, 875 g ai/ha or less, 850 g ai/ha or less, 825 g ai/ha or
less, 800 g ai/ha or less, 775 g ai/ha or less, 750 g ai/ha or
less, 725 g ai/ha or less, 700 g ai/ha or less, 675 g ai/ha or
less, 650 g ai/ha or less, 625 g ai/ha or less, 600 g ai/ha or
less, 575 g ai/ha or less, 550 g ai/ha or less, 525 g ai/ha or
less, 500 g ai/ha or less, 475 g ai/ha or less, 450 g ai/ha or
less, 425 g ai/ha or less, 400 g ai/ha or less, 380 g ai/ha or
less, 360 g ai/ha or less, 340 g ai/ha or less, 320 g ai/ha or
less, or 300 g ai/ha or less).
[0318] The benzofenap or an agriculturally acceptable salt thereof
can be applied to vegetation or an area adjacent the vegetation or
applied to soil or water to prevent the emergence or growth of
vegetation in an amount ranging from any of the minimum values
described above to any of the maximum values described above. In
some embodiments, the benzofenap or an agriculturally acceptable
salt thereof is applied to vegetation or an area adjacent the
vegetation or applied to soil or water to prevent the emergence or
growth of vegetation in an amount of 300-1000 g ai/ha (e.g.,
350-1000 g ai/ha, 400-1000 g ai/ha, 450-1000 g ai/ha, 500-1000 g
ai/ha, 550-1000 g ai/ha, 600-1000 g ai/ha, 600-950 g ai/ha, 600-900
g ai/ha, 650-1000 g ai/ha, 700-1000 g ai/ha, 750-1000 g ai/ha,
800-1000 g ai/ha, 800-950 g ai/ha, or 800-900 g ai/ha).
[0319] Bicyclopyrone
[0320] Compositions and methods of the present disclosure can
include bicyclopyrone or an agriculturally acceptable salt thereof.
Bicyclopyrone, shown below, is
4-hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridinyl-
]carbonyl]bicyclo[3.2.1]oct-3-en-2-one. According to the online
edition of The Pesticide Manual, bicyclopyrone is a herbicide for
use in pre- and early post emergence applications in maize (ca.
50-200 g/ha) to control broad-leaved weeds such as Amaranthus
palmeri (palmer amaranth), Ambrosia artemisiifolia (common
ragweed), Ambrosia trifida (giant ragweed), Chenopodium album
(common lambsquarters), Raphanus raphanistrum (wild radish),
Stellaria media (common chickweed), Xanthium strumarium (common
cocklebur) and grasses such as Eriochloa villosa (woolly cupgrass).
It is under development for post-emergence use (37.5-50 g/ha) in
cereals and pre- and early post-emergence use (up to 300 g/ha) in
sugar cane.
##STR00038##
[0321] The bicyclopyrone or agriculturally acceptable salt thereof
can be applied to vegetation or an area adjacent the vegetation or
applied to soil or water to prevent the emergence or growth of
vegetation in an amount sufficient to induce a herbicidal effect.
In some embodiments, the bicyclopyrone or agriculturally acceptable
salt thereof is applied to vegetation or an area adjacent the
vegetation or applied to soil or water to prevent the emergence or
growth of vegetation in an amount of 20 g ai/ha or more (e.g., 25 g
ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha
or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or
more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more,
75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g
ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g
ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g
ai/ha or more, 160 g ai/ha or more, 170 g ai/ha or more, 180 g
ai/ha or more, 190 g ai/ha or more, 200 g ai/ha or more, 220 g
ai/ha or more, 240 g ai/ha or more, 260 g ai/ha or more, 280 g
ai/ha or more, 300 g ai/ha or more, 320 g ai/ha or more, 340 g
ai/ha or more, 360 g ai/ha or more, 380 g ai/ha or more, or 400 g
ai/ha).
[0322] In some embodiments, the bicyclopyrone or agriculturally
acceptable salt thereof is applied to vegetation or an area
adjacent the vegetation or applied to soil or water to prevent the
emergence or growth of vegetation in an amount of 401 g ai/ha or
less (e.g., 400 g ai/ha or less, 380 g ai/ha or less, 360 g ai/ha
or less, 340 g ai/ha or less, 320 g ai/ha or less, 300 g ai/ha or
less, 280 g ai/ha or less, 260 g ai/ha or less, 240 g ai/ha or
less, 220 g ai/ha or less, 200 g ai/ha or less, 190 g ai/ha or
less, 180 g ai/ha or less, 170 g ai/ha or less, 160 g ai/ha or
less, 150 g ai/ha or less, 140 g ai/ha or less, 130 g ai/ha or
less, 120 g ai/ha or less, 110 g ai/ha or less, 100 g ai/ha or
less, 90 g ai/ha or less, 85 g ai/ha or less, 80 g ai/ha or less,
75 g ai/ha or less, 70 g ai/ha or less, 65 g ai/ha or less, 60 g
ai/ha or less, 55 g ai/ha or less, 50 g ai/ha or less, 45 g ai/ha
or less, 40 g ai/ha or less, 35 g ai/ha or less, 30 g ai/ha or
less, 25 g ai/ha or less, or 20 g ai/ha or less).
[0323] The bicyclopyrone or an agriculturally acceptable salt
thereof can be applied to vegetation or an area adjacent the
vegetation or applied to soil or water to prevent the emergence or
growth of vegetation in an amount ranging from any of the minimum
values described above to any of the maximum values described
above. In some embodiments, the bicyclopyrone or agriculturally
acceptable salt thereof is applied to vegetation or an area
adjacent the vegetation or applied to soil or water to prevent the
emergence or growth of vegetation in an amount of 20-400 g ai/ha
(e.g., 30-400 g ai/ha, 40-400 g ai/ha, 50-400 g ai/ha, 50-350 g
ai/ha, 50-300 g ai/ha, 75-300 g ai/ha, 100-300 g ai/ha, 200-300 g
ai/ha, 50-200 g ai/ha, 30-100 g ai/ha, 30-75 g ai/ha, 30-65 g
ai/ha, or 30-55 g ai/ha).
[0324] Fenquinotrione
[0325] Fenquinotrione, shown below, is
2-[[8-chloro-3,4-dihydro-4-(4-methoxyphenyl)-3-oxo-2-quinoxalinyl]carbony-
l]-1,3-cyclohexanedione. According to the online edition of The
Pesticide Manual, fenquinotrione is a herbicide under development
for use on rice (Kumiai).
##STR00039##
[0326] Isoxachlortole
[0327] Isoxachlortole, shown below, is
[4-chloro-2-(methylsulfonyl)phenyl](5-cyclopropyl-4-isoxazolyl)methanone.
According to the online edition of The Pesticide Manual,
isoxachlortole is a herbicide that was evaluated by
Rhone-Poulenc.
##STR00040##
[0328] Isoxaflutole
[0329] Isoxaflutole, shown below, is
(5-cyclopropyl-4-isoxazolyl)[2-(methylsulfonyl)-4-(trifluoromethyl)phenyl-
]methanone. Its herbicidal activity is exemplified in The Pesticide
Manual. Exemplary uses of isoxaflutole include its use as a
broad-spectrum grass and broadleaf weed control in maize and sugar
cane, applied at 75-140 g/ha pre-emergence or pre-plant; the
spectrum can be enhanced by mixture with other active
ingredients.
##STR00041##
[0330] In some embodiments, isoxaflutole can be provided as an
agriculturally acceptable salt of isoxaflutole.
[0331] The isoxaflutole or agriculturally acceptable salt thereof
can be applied to vegetation or an area adjacent the vegetation or
applied to soil or water to prevent the emergence or growth of
vegetation in an amount sufficient to induce a herbicidal effect.
In some embodiments, the isoxaflutole or agriculturally acceptable
salt thereof is applied to vegetation or an area adjacent the
vegetation or applied to soil or water to prevent the emergence or
growth of vegetation in an amount of 20 g ai/ha or more (e.g., 25 g
ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha
or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or
more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more,
75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g
ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g
ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g
ai/ha or more, 160 g ai/ha or more, 170 g ai/ha or more, 180 g
ai/ha or more, 190 g ai/ha or more, 200 g ai/ha or more, 220 g
ai/ha or more, 240 g ai/ha or more, 260 g ai/ha or more, 280 g
ai/ha or more, or 300 g ai/ha or more).
[0332] In some embodiments, the isoxaflutole or agriculturally
acceptable salt thereof is applied to vegetation or an area
adjacent the vegetation or applied to soil or water to prevent the
emergence or growth of vegetation in an amount of 301 g ai/ha or
less (e.g., 300 g ai/ha or less, 280 g ai/ha or less, 260 g ai/ha
or less, 240 g ai/ha or less, 220 g ai/ha or less, 200 g ai/ha or
less, 190 g ai/ha or less, 180 g ai/ha or less, 170 g ai/ha or
less, 160 g ai/ha or less, 150 g ai/ha or less, 140 g ai/ha or
less, 130 g ai/ha or less, 120 g ai/ha or less, 110 g ai/ha or
less, 100 g ai/ha or less, 90 g ai/ha or less, 85 g ai/ha or less,
80 g ai/ha or less, 75 g ai/ha or less, 70 g ai/ha or less, 65 g
ai/ha or less, 60 g ai/ha or less, 55 g ai/ha or less, 50 g ai/ha
or less, 45 g ai/ha or less, 40 g ai/ha or less, 35 g ai/ha or
less, 30 g ai/ha or less, or 25 g ai/ha or less).
[0333] The isoxaflutole or an agriculturally acceptable salt
thereof can be applied to vegetation or an area adjacent the
vegetation or applied to soil or water to prevent the emergence or
growth of vegetation in an amount ranging from any of the minimum
values described above to any of the maximum values described
above. In some embodiments, the isoxaflutole or agriculturally
acceptable salt thereof is applied to vegetation or an area
adjacent the vegetation or applied to soil or water to prevent the
emergence or growth of vegetation in an amount of 25-300 g ai/ha
(e.g., 30-300 g ai/ha, 40-300 g ai/ha, 50-300 g ai/ha, 60-300 g
ai/ha, 70-300 g ai/ha, 70-275 g ai/ha, 75-250 g ai/ha, 75-225 g
ai/ha, 75-200 g ai/ha, 75-175 g ai/ha, 75-150 g ai/ha, 75-125 g
ai/ha, 75-100 g ai/ha, 100-300 g ai/ha, 150-300 g ai/ha, 200-300 g
ai/ha, 50-200 g ai/ha, 25-100 g ai/ha, 25-75 g ai/ha, or 25-50 g
ai/ha).
[0334] Mesotrione
[0335] Mesotrione, shown below, is
2-[4-(methylsulfonyl)-2-nitrobenzoyl]-1,3-cyclohexanedione. Its
herbicidal activity is exemplified in The Pesticide Manual.
Exemplary uses of mesotrione include its use pre-emergence (at
100-225 g/ha) and post-emergence (at 70-150 g/ha) to control of
broadleaf weeds, such as Xanthium strumarium, Ambrosia trifida,
Abutilon theophrasti, and Chenopodium, Amaranthus and Polygonum
spp., and some grass weeds in maize.
##STR00042##
[0336] In some embodiments, mesotrione can be provided as an
agriculturally acceptable salt of mesotrione.
[0337] The mesotrione or agriculturally acceptable salt thereof can
be applied to vegetation or an area adjacent the vegetation or
applied to soil or water to prevent the emergence or growth of
vegetation in an amount sufficient to induce a herbicidal effect.
In some embodiments, the mesotrione or agriculturally acceptable
salt thereof is applied to vegetation or an area adjacent the
vegetation or applied to soil or water to prevent the emergence or
growth of vegetation in an amount of 20 g ai/ha or more (e.g., 25 g
ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha
or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or
more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more,
75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g
ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g
ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g
ai/ha or more, 160 g ai/ha or more, 170 g ai/ha or more, 180 g
ai/ha or more, 190 g ai/ha or more, 200 g ai/ha or more, 220 g
ai/ha or more, 240 g ai/ha or more, 260 g ai/ha or more, 280 g
ai/ha or more, or 300 g ai/ha or more).
[0338] In some embodiments, the mesotrione or agriculturally
acceptable salt thereof is applied to vegetation or an area
adjacent the vegetation or applied to soil or water to prevent the
emergence or growth of vegetation in an amount of 301 g ai/ha or
less (e.g., 300 g ai/ha or less, 280 g ai/ha or less, 260 g ai/ha
or less, 240 g ai/ha or less, 220 g ai/ha or less, 200 g ai/ha or
less, 190 g ai/ha or less, 180 g ai/ha or less, 170 g ai/ha or
less, 160 g ai/ha or less, 150 g ai/ha or less, 140 g ai/ha or
less, 130 g ai/ha or less, 120 g ai/ha or less, 110 g ai/ha or
less, 100 g ai/ha or less, 90 g ai/ha or less, 85 g ai/ha or less,
80 g ai/ha or less, 75 g ai/ha or less, 70 g ai/ha or less, 65 g
ai/ha or less, 60 g ai/ha or less, 55 g ai/ha or less, 50 g ai/ha
or less, 45 g ai/ha or less, 40 g ai/ha or less, 35 g ai/ha or
less, 30 g ai/ha or less, or 25 g ai/ha or less).
[0339] The mesotrione or an agriculturally acceptable salt thereof
can be applied to vegetation or an area adjacent the vegetation or
applied to soil or water to prevent the emergence or growth of
vegetation in an amount ranging from any of the minimum values
described above to any of the maximum values described above. In
some embodiments, the mesotrione or agriculturally acceptable salt
thereof is applied to vegetation or an area adjacent the vegetation
or applied to soil or water to prevent the emergence or growth of
vegetation in an amount of 25-300 g ai/ha (e.g., 30-300 g ai/ha,
40-300 g ai/ha, 50-300 g ai/ha, 60-300 g ai/ha, 70-300 g ai/ha,
70-275 g ai/ha, 70-250 g ai/ha, 70-225 g ai/ha, 70-200 g ai/ha,
70-175 g ai/ha, 70-150 g ai/ha, 70-125 g ai/ha, 70-100 g ai/ha,
80-300 g ai/ha, 80-275 g ai/ha, 90-250 g ai/ha, 100-225 g ai/ha,
110-200 g ai/ha, 120-175 g ai/ha, 130-150 g ai/ha, 25-75 g ai/ha,
or 25-50 g ai/ha).
[0340] Pyrasulfotole
[0341] Pyrasulfotole, shown below, is
(5-hydroxy-1,3-dimethyl-1H-pyrazol-4-yl)[2-(methylsulfonyl)-4-(trifluorom-
ethyl)phenyl]methanone. Its herbicidal activity is exemplified in
The Pesticide Manual. Exemplary uses of pyrasulfotole include its
use in mixtures with mefenpyr-diethyl and bromoxynil, bromoxynil
and thiencarbazone-methyl, bromoxynil and fenoxaprop-p-ethyl or
MCPA ester, for post-emergence control of broadleaf weeds in
cereals, applied at a rate of 31-50 g/ha.
##STR00043##
[0342] In some embodiments, pyrasulfotole can be provided as an
agriculturally acceptable salt of pyrasulfotole.
[0343] The pyrasulfotole or agriculturally acceptable salt thereof
can be applied to vegetation or an area adjacent the vegetation or
applied to soil or water to prevent the emergence or growth of
vegetation in an amount sufficient to induce a herbicidal effect.
In some embodiments, the pyrasulfotole or agriculturally acceptable
salt thereof is applied to vegetation or an area adjacent the
vegetation or applied to soil or water to prevent the emergence or
growth of vegetation in an amount of 1.9 g ai/ha or more (e.g., 2.5
g ai/ha or more, 3 g ai/ha or more, 3.25 g ai/ha or more, 3.5 g
ai/ha or more, 3.75 g ai/ha or more, 4 g ai/ha or more, 4.5 g ai/ha
or more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 8
g ai/ha or more, 9 g ai/ha or more, 9.5 g ai/ha or more, 10 g ai/ha
or more, 10.5 g ai/ha or more, 11 g ai/ha or more, 11.5 g ai/ha or
more, 12 g ai/ha or more, 12.5 g ai/ha or more, 13 g ai/ha or more,
13.5 g ai/ha or more, 14 g ai/ha or more, 14.5 g ai/ha or more, 15
g ai/ha or more, 15.25 g ai/ha or more, 15.5 g ai/ha or more, 15.75
g ai/ha or more, 16 g ai/ha or more, 16.25 g ai/ha or more, 16.5 g
ai/ha or more, 16.75 g ai/ha or more, 17 g ai/ha or more, 17.25 g
ai/ha or more, 17.5 g ai/ha or more, 17.75 g ai/ha or more, 18 g
ai/ha or more, 18.25 g ai/ha or more, 18.5 g ai/ha or more, 19.5 g
ai/ha or more, 20 g ai/ha or more, 22 g ai/ha or more, 24 g ai/ha
or more, 26 g ai/ha or more, 28 g ai/ha or more, 30 g ai/ha or
more, 33 g ai/ha or more, 36 g ai/ha or more, 39 g ai/ha or more,
42 g ai/ha or more, 45 g ai/ha or more, or 50 g ai/ha or more).
[0344] In some embodiments, the pyrasulfotole or agriculturally
acceptable salt thereof is applied to vegetation or an area
adjacent the vegetation or applied to soil or water to prevent the
emergence or growth of vegetation in an amount of 51 g ai/ha or
less (e.g., 50 g ai/ha or less, 45 g ai/ha or less, 42 g ai/ha or
less, 40 g ai/ha or less, 38 g ai/ha or less, 35 g ai/ha or less,
32 g ai/ha or less, 30 g ai/ha or less, 28 g ai/ha or less, 26 g
ai/ha or less, 24 g ai/ha or less, 22 g ai/ha or less, 20 g ai/ha
or less, 19 g ai/ha or less, 18.5 g ai/ha or less, 18.25 g ai/ha or
less, 18 g ai/ha or less, 17.75 g ai/ha or less, 17.5 g ai/ha or
less, 17.25 g ai/ha or less, 17 g ai/ha or less, 16.75 g ai/ha or
less, 16.5 g ai/ha or less, 16.25 g ai/ha or less, 16 g ai/ha or
less, 15.75 g ai/ha or less, 15.5 g ai/ha or less, 15.25 g ai/ha or
less, 15 g ai/ha or less, 14.5 g ai/ha or less, 14 g ai/ha or less,
13.5 g ai/ha or less, 13 g ai/ha or less, 12.5 g ai/ha or less, 12
g ai/ha or less, 11.5 g ai/ha or less, 11 g ai/ha or less, 10.5 g
ai/ha or less, 10 g ai/ha or less, 9.5 g ai/ha or less, 9 g ai/ha
or less, 8 g ai/ha or less, 7 g ai/ha or less, 6 g ai/ha or less, 5
g ai/ha or less, 4.5 g ai/ha or less, 4 g ai/ha or less, 3.5 g
ai/ha or less, 3.25 g ai/ha or less, 3 g ai/ha or less, or 2.5 g
ai/ha or less).
[0345] The pyrasulfotole or an agriculturally acceptable salt
thereof can be applied to vegetation or an area adjacent the
vegetation or applied to soil or water to prevent the emergence or
growth of vegetation in an amount ranging from any of the minimum
values described above to any of the maximum values described
above. In some embodiments, the pyrasulfotole or agriculturally
acceptable salt thereof is applied to vegetation or an area
adjacent the vegetation or applied to soil or water to prevent the
emergence or growth of vegetation in an amount of 1.9-51 g ai/ha
(e.g., 1.9-45 g ai/ha, 1.9-40 g ai/ha, 1.9-35 g ai/ha, 1.9-30 g
ai/ha, 1.9-25 g ai/ha, 1.9-20 g ai/ha, 1.9-18.75 g ai/ha 2.5-18 g
ai/ha, 2.5-17 g ai/ha, 2.75-16 g ai/ha, 2.75-18.75 g ai/ha, 3-18 g
ai/ha, 3.25-17 g ai/ha, 3.25-16 g ai/ha, 3.5-18.75 g ai/ha, 3.5-18
g ai/ha, 3.5-17 g ai/ha, 3.5-16 g ai/ha, 3.5-15 g ai/ha, 3.5-14 g
ai/ha, 20-51 g ai/ha, 25-51 g ai/ha, 30-51 g ai/ha, 35-51 g ai/ha,
40-51 g ai/ha, or 45-51 g ai/ha).
[0346] In some aspects, composition may include an HPPD inhibitor
and a third herbicide. For example, in various aspects,
compositions may include the compound defined by Formula (I), an
HPPD inhibitor, and a third herbicide (e.g., bromoxynil). Thus, in
some aspects, compositions may include the compound of Formula (I),
pyransulfotole, and bromonxynil. In some aspects, the ratio of
bromoxynil and pyransulfotole may be between about 10:1 to about
1:10, between about 7:1 to about 1:1, or between about 6:1 to about
5:1.
[0347] Pyrazolynate
[0348] Pyrazolynate, shown below, is
(2,4-dichlorophenyl)[1,3-dimethyl-5-[[(4-methylphenyl)sulfonyl]oxy]-1H-py-
razol-4-yl]methanone. Its herbicidal activity is exemplified in The
Pesticide Manual. Exemplary uses of pyrazolynate include its use to
control grasses, sedges, Potamogeton distinctus, Sagittaria
pygmaea, Sagittaria trifolia and Alisma canaliculatum in paddy
rice, at 3-4 kg/ha.
##STR00044##
[0349] The pyrazolynate can be applied to vegetation or an area
adjacent the vegetation or applied to soil or water to prevent the
emergence or growth of vegetation in an amount sufficient to induce
a herbicidal effect. In some embodiments, the pyrazolynate is
applied to vegetation or an area adjacent the vegetation or applied
to soil or water to prevent the emergence or growth of vegetation
in an amount of 200 g ai/ha or more (e.g., 300 g ai/ha or more, 400
g ai/ha or more, 500 g ai/ha or more, 600 g ai/ha or more, 700 g
ai/ha or more, 800 g ai/ha or more, 900 g ai/ha or more, 1000 g
ai/ha or more, 1200 g ai/ha or more, 1400 g ai/ha or more, 1600 g
ai/ha or more, 1800 g ai/ha or more, 2000 g ai/ha or more, 2200 g
ai/ha or more, 2400 g ai/ha or more, 2600 g ai/ha or more, 2800 g
ai/ha or more, 3000 g ai/ha or more, 3200 g ai/ha or more, 3400 g
ai/ha or more, 3600 g ai/ha or more, 3800 g ai/ha or more, 4000 g
ai/ha or more, 4200 g ai/ha or more, or 4400 g ai/ha or more).
[0350] In some embodiments, the pyrazolynate is applied to
vegetation or an area adjacent the vegetation or applied to soil or
water to prevent the emergence or growth of vegetation in an amount
of 4500 g ai/ha or less (e.g., 4400 g ai/ha or less, 4200 g ai/ha
or less, 4000 g ai/ha or less, 3800 g ai/ha or less, 3600 g ai/ha
or less, 3400 g ai/ha or less, 3200 g ai/ha or less, 3000 g ai/ha
or less, 2800 g ai/ha or less, 2600 g ai/ha or less, 2400 g ai/ha
or less, 2200 g ai/ha or less, 2000 g ai/ha or less, 1800 g ai/ha
or less, 1600 g ai/ha or less, 1400 g ai/ha or less, 1200 g ai/ha
or less, 1000 g ai/ha or less, 900 g ai/ha or less, 800 g ai/ha or
less, 700 g ai/ha or less, 600 g ai/ha or less, 500 g ai/ha or
less, 400 g ai/ha or less, 300 g ai/ha or less, or 200 g ai/ha or
less).
[0351] The pyrazolynate can be applied to vegetation or an area
adjacent the vegetation or applied to soil or water to prevent the
emergence or growth of vegetation in an amount ranging from any of
the minimum values described above to any of the maximum values
described above. In some embodiments, the pyrazolynate is applied
to vegetation or an area adjacent the vegetation or applied to soil
or water to prevent the emergence or growth of vegetation in an
amount of 200-4500 g ai/ha (e.g., 200-400 g ai/ha, 400-600 g ai/ha,
600-800 g ai/ha, 800-1000 g ai/ha, 1000-1500 g ai/ha, 1500-2000 g
ai/ha, 2000-2500 g ai/ha, 2500-3000 g ai/ha, 3000-3500 g ai/ha,
3500-4000 g ai/ha, or 4000-4500 g ai/ha).
[0352] Pyrazoxyfen
[0353] Pyrazoxyfen, shown below, is
2-[[4-(2,4-dichlorobenzoyl)-1,3-dimethyl-1H-pyrazol-5-yl]oxy]-1-phenyleth-
anone. Its herbicidal activity is exemplified in The Pesticide
Manual. Exemplary uses of pyrazoxyfen include its use pre- or
post-weed emergence, at 3 kg/ha, in transplanted paddy rice, to
control annual and perennial weeds.
##STR00045##
[0354] The pyrazoxyfen can be applied to vegetation or an area
adjacent the vegetation or applied to soil or water to prevent the
emergence or growth of vegetation in an amount sufficient to induce
a herbicidal effect. In some embodiments, the pyrazoxyfen is
applied to vegetation or an area adjacent the vegetation or applied
to soil or water to prevent the emergence or growth of vegetation
in an amount of 200 g ai/ha or more (e.g., 300 g ai/ha or more, 400
g ai/ha or more, 500 g ai/ha or more, 600 g ai/ha or more, 700 g
ai/ha or more, 800 g ai/ha or more, 900 g ai/ha or more, 1000 g
ai/ha or more, 1200 g ai/ha or more, 1400 g ai/ha or more, 1600 g
ai/ha or more, 1800 g ai/ha or more, 2000 g ai/ha or more, 2200 g
ai/ha or more, 2400 g ai/ha or more, 2600 g ai/ha or more, 2800 g
ai/ha or more, 3000 g ai/ha or more, 3200 g ai/ha or more, or 3400
g ai/ha or more).
[0355] In some embodiments, the pyrazoxyfen is applied to
vegetation or an area adjacent the vegetation or applied to soil or
water to prevent the emergence or growth of vegetation in an amount
of 3500 g ai/ha or less (e.g., 3400 g ai/ha or less, 3200 g ai/ha
or less, 3000 g ai/ha or less, 2800 g ai/ha or less, 2600 g ai/ha
or less, 2400 g ai/ha or less, 2200 g ai/ha or less, 2000 g ai/ha
or less, 1800 g ai/ha or less, 1600 g ai/ha or less, 1400 g ai/ha
or less, 1200 g ai/ha or less, 1000 g ai/ha or less, 900 g ai/ha or
less, 800 g ai/ha or less, 700 g ai/ha or less, 600 g ai/ha or
less, 500 g ai/ha or less, 400 g ai/ha or less, 300 g ai/ha or
less, or 200 g ai/ha or less).
[0356] The pyrazoxyfen can be applied to vegetation or an area
adjacent the vegetation or applied to soil or water to prevent the
emergence or growth of vegetation in an amount ranging from any of
the minimum values described above to any of the maximum values
described above. In some embodiments, the pyrazoxyfen is applied to
vegetation or an area adjacent the vegetation or applied to soil or
water to prevent the emergence or growth of vegetation in an amount
of 200-3500 g ai/ha (e.g., 200-400 g ai/ha, 400-600 g ai/ha,
600-800 g ai/ha, 800-1000 g ai/ha, 1000-1500 g ai/ha, 1500-2000 g
ai/ha, 2000-2500 g ai/ha, 2500-3000 g ai/ha, or 3000-3500 g
ai/ha).
[0357] Sulcotrione
[0358] Sulcotrione, shown below, is
2-[2-chloro-4-(methylsulfonyl)benzoyl]-1,3-cyclohexanedione. Its
herbicidal activity is exemplified in The Pesticide Manual.
Exemplary uses of sulcotrione include its use to control broadleaf
weeds and grasses post-emergence in maize, at up to 450 g/ha, and
in sugar cane, at 200-300 g/ha.
##STR00046##
[0359] In some embodiments, sulcotrione can be provided as an
agriculturally acceptable salt of sulcotrione.
[0360] The sulcotrione or agriculturally acceptable salt thereof
can be applied to vegetation or an area adjacent the vegetation or
applied to soil or water to prevent the emergence or growth of
vegetation in an amount sufficient to induce a herbicidal effect.
In some embodiments, the sulcotrione or agriculturally acceptable
salt thereof is applied to vegetation or an area adjacent the
vegetation or applied to soil or water to prevent the emergence or
growth of vegetation in an amount of 50 g ai/ha or more (e.g., 55 g
ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha
or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or
more, 90 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more,
120 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150
g ai/ha or more, 160 g ai/ha or more, 170 g ai/ha or more, 180 g
ai/ha or more, 190 g ai/ha or more, 200 g ai/ha or more, 220 g
ai/ha or more, 240 g ai/ha or more, 260 g ai/ha or more, 280 g
ai/ha or more, 300 g ai/ha or more, 320 g ai/ha or more, 340 g
ai/ha or more, 360 g ai/ha or more, 380 g ai/ha or more, 400 g
ai/ha or more, 420 g ai/ha or more, 440 g ai/ha or more, 460 g
ai/ha or more, 480 g ai/ha or more, 500 g ai/ha or more, 520 g
ai/ha or more, 540 g ai/ha or more, 560 g ai/ha or more, 580 g
ai/ha or more, or 600 g ai/ha or more).
[0361] In some embodiments, the sulcotrione or agriculturally
acceptable salt thereof is applied to vegetation or an area
adjacent the vegetation or applied to soil or water to prevent the
emergence or growth of vegetation in an amount of 600 g ai/ha or
less (e.g., 580 g ai/ha or less, 560 g ai/ha or less, 540 g ai/ha
or less, 520 g ai/ha or less, 500 g ai/ha or less, 480 g ai/ha or
less, 460 g ai/ha or less, 440 g ai/ha or less, 420 g ai/ha or
less, 400 g ai/ha or less, 380 g ai/ha or less, 360 g ai/ha or
less, 340 g ai/ha or less, 320 g ai/ha or less, 300 g ai/ha or
less, 280 g ai/ha or less, 260 g ai/ha or less, 240 g ai/ha or
less, 220 g ai/ha or less, 200 g ai/ha or less, 190 g ai/ha or
less, 180 g ai/ha or less, 170 g ai/ha or less, 160 g ai/ha or
less, 150 g ai/ha or less, 140 g ai/ha or less, 130 g ai/ha or
less, 120 g ai/ha or less, 110 g ai/ha or less, 100 g ai/ha or
less, 90 g ai/ha or less, 85 g ai/ha or less, 80 g ai/ha or less,
75 g ai/ha or less, 70 g ai/ha or less, 65 g ai/ha or less, 60 g
ai/ha or less, 55 g ai/ha or less, or 50 g ai/ha or less).
[0362] The sulcotrione or an agriculturally acceptable salt thereof
can be applied to vegetation or an area adjacent the vegetation or
applied to soil or water to prevent the emergence or growth of
vegetation in an amount ranging from any of the minimum values
described above to any of the maximum values described above. In
some embodiments, the sulcotrione or agriculturally acceptable salt
thereof is applied to vegetation or an area adjacent the vegetation
or applied to soil or water to prevent the emergence or growth of
vegetation in an amount of 50-600 g ai/ha (e.g., 100-600 g ai/ha,
150-600 g ai/ha, 200-600 g ai/ha, 300-600 g ai/ha, 400-600 g ai/ha,
300-500 g ai/ha, 250-500 g ai/ha, 250-450 g ai/ha, 275-450 g ai/ha,
300-450 g ai/ha, 325-450 g ai/ha, 350-450 g ai/ha, 375-450 g ai/ha,
400-450 g ai/ha, 50-400 g ai/ha, 100-400 g ai/ha, 150-400 g ai/ha,
175-400 g ai/ha, 175-350 g ai/ha, 175-325 g ai/ha, 175-300 g ai/ha,
200-300 g ai/ha, 225-300 g ai/ha, 250-300 g ai/ha, or 275-300 g
ai/ha,).
[0363] Tembotrione
[0364] Tembotrione, shown below, is
2-[2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl]--
1,3-cyclohexanedione. Its herbicidal activity is exemplified in The
Pesticide Manual. Exemplary uses of tembotrione include its use for
post-emergence control a wide range of dicotyledonous and
monocotyledonous weed species in maize, with a maximum dose rate
per season of 100 g/ha, applied either as one single dose or two
sequential, partial doses.
##STR00047##
[0365] In some embodiments, tembotrione can be provided as an
agriculturally acceptable salt of tembotrione.
[0366] The tembotrione or agriculturally acceptable salt thereof
can be applied to vegetation or an area adjacent the vegetation or
applied to soil or water to prevent the emergence or growth of
vegetation in an amount sufficient to induce a herbicidal effect.
In some embodiments, the tembotrione or agriculturally acceptable
salt thereof is applied to vegetation or an area adjacent the
vegetation or applied to soil or water to prevent the emergence or
growth of vegetation in an amount of 1 g ai/ha or more (e.g., 2 g
ai/ha or more, 4 g ai/ha or more, 6 g ai/ha or more, 8 g ai/ha or
more, 10 g ai/ha or more, 15 g ai/ha or more, 20 g ai/ha or more,
25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g
ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha
or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or
more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more,
90 g ai/ha or more, 95 g ai/ha or more, 100 g ai/ha or more, 110 g
ai/ha or more, 120 g ai/ha or more, 130 g ai/ha or more, 140 g
ai/ha or more, 150 g ai/ha or more, 160 g ai/ha or more, 170 g
ai/ha or more, 180 g ai/ha or more, 190 g ai/ha or more, or 200 g
ai/ha or more.
[0367] In some embodiments, the tembotrione or agriculturally
acceptable salt thereof is applied to vegetation or an area
adjacent the vegetation or applied to soil or water to prevent the
emergence or growth of vegetation in an amount of 200 g ai/ha or
less (e.g., 190 g ai/ha or less, 180 g ai/ha or less, 170 g ai/ha
or less, 160 g ai/ha or less, 150 g ai/ha or less, 140 g ai/ha or
less, 130 g ai/ha or less, 120 g ai/ha or less, 110 g ai/ha or
less, 100 g ai/ha or less, 95 g ai/ha or less, 90 g ai/ha or less,
85 g ai/ha or less, 80 g ai/ha or less, 75 g ai/ha or less, 70 g
ai/ha or less, 65 g ai/ha or less, 60 g ai/ha or less, 55 g ai/ha
or less, 50 g ai/ha or less, 45 g ai/ha or less, 40 g ai/ha or
less, 35 g ai/ha or less, 30 g ai/ha or less, 25 g ai/ha or less,
20 g ai/ha or less, 15 g ai/ha or less, 10 g ai/ha or less, 9 g
ai/ha or less, 8 g ai/ha or less, 7 g ai/ha or less, 6 g ai/ha or
less, 5 g ai/ha or less, 4.5 g ai/ha or less, 4 g ai/ha or less,
3.5 g ai/ha or less, 3 g ai/ha or less, 2.5 g ai/ha or less, 2 g
ai/ha or less, 1.5 g ai/ha or less, or 1 g ai/ha or less).
[0368] The tembotrione or an agriculturally acceptable salt thereof
can be applied to vegetation or an area adjacent the vegetation or
applied to soil or water to prevent the emergence or growth of
vegetation in an amount ranging from any of the minimum values
described above to any of the maximum values described above. In
some embodiments, the tembotrione or agriculturally acceptable salt
thereof is applied to vegetation or an area adjacent the vegetation
or applied to soil or water to prevent the emergence or growth of
vegetation in an amount of 1-200 g ai/ha (e.g., 1-175 g ai/ha,
1-150 g ai/ha, 1-100 g ai/ha, 1-75 g ai/ha, 1-50 g ai/ha, 1-25 g
ai/ha, 1-15 g ai/ha, 1-10 g ai/ha, 5-20 g ai/ha, 10-30 g ai/ha,
20-40 g ai/ha, 30-50 g ai/ha, 40-60 g ai/ha, 50-70 g ai/ha, 60-80 g
ai/ha, 70-90 g ai/ha, 80-100 g ai/ha, 90-110 g ai/ha, 100-120 g
ai/ha, 110-130 g ai/ha, 120-140 g ai/ha, or 130-150 g ai/ha).
[0369] Tefuryltrione
[0370] Tefuryltrione, shown below, is
2-[2-chloro-4-(methylsulfonyl)-3-[[(tetrahydro-2-furanyl)methoxy]methyl]b-
enzoyl]-1,3-cyclohexanedione. Its herbicidal activity is
exemplified in The Pesticide Manual. Exemplary uses of
tefuryltrione include its use for post-emergence control a wide
range of dicotyledonous and monocotyledonous weed species in maize,
with a maximum dose rate per season of 100 g/ha, applied either as
one single dose or two sequential, partial doses.
##STR00048##
[0371] In some embodiments, tefuryltrione can be provided as an
agriculturally acceptable salt of tefuryltrione.
[0372] The tefuryltrione or agriculturally acceptable salt thereof
can be applied to vegetation or an area adjacent the vegetation or
applied to soil or water to prevent the emergence or growth of
vegetation in an amount sufficient to induce a herbicidal effect.
In some embodiments, the tefuryltrione or agriculturally acceptable
salt thereof is applied to vegetation or an area adjacent the
vegetation or applied to soil or water to prevent the emergence or
growth of vegetation in an amount of 1 g ai/ha or more (e.g., 2 g
ai/ha or more, 4 g ai/ha or more, 6 g ai/ha or more, 8 g ai/ha or
more, 10 g ai/ha or more, 15 g ai/ha or more, 20 g ai/ha or more,
25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g
ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha
or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or
more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more,
90 g ai/ha or more, 95 g ai/ha or more, 100 g ai/ha or more, 110 g
ai/ha or more, 120 g ai/ha or more, 130 g ai/ha or more, 140 g
ai/ha or more, 150 g ai/ha or more, 160 g ai/ha or more, 170 g
ai/ha or more, 180 g ai/ha or more, 190 g ai/ha or more, or 200 g
ai/ha or more.
[0373] In some embodiments, the tefuryltrione or agriculturally
acceptable salt thereof is applied to vegetation or an area
adjacent the vegetation or applied to soil or water to prevent the
emergence or growth of vegetation in an amount of 200 g ai/ha or
less (e.g., 190 g ai/ha or less, 180 g ai/ha or less, 170 g ai/ha
or less, 160 g ai/ha or less, 150 g ai/ha or less, 140 g ai/ha or
less, 130 g ai/ha or less, 120 g ai/ha or less, 110 g ai/ha or
less, 100 g ai/ha or less, 95 g ai/ha or less, 90 g ai/ha or less,
85 g ai/ha or less, 80 g ai/ha or less, 75 g ai/ha or less, 70 g
ai/ha or less, 65 g ai/ha or less, 60 g ai/ha or less, 55 g ai/ha
or less, 50 g ai/ha or less, 45 g ai/ha or less, 40 g ai/ha or
less, 35 g ai/ha or less, 30 g ai/ha or less, 25 g ai/ha or less,
20 g ai/ha or less, 15 g ai/ha or less, 10 g ai/ha or less, 9 g
ai/ha or less, 8 g ai/ha or less, 7 g ai/ha or less, 6 g ai/ha or
less, 5 g ai/ha or less, 4.5 g ai/ha or less, 4 g ai/ha or less,
3.5 g ai/ha or less, 3 g ai/ha or less, 2.5 g ai/ha or less, 2 g
ai/ha or less, 1.5 g ai/ha or less, or 1 g ai/ha or less).
[0374] The tefuryltrione or an agriculturally acceptable salt
thereof can be applied to vegetation or an area adjacent the
vegetation or applied to soil or water to prevent the emergence or
growth of vegetation in an amount ranging from any of the minimum
values described above to any of the maximum values described
above. In some embodiments, the tefuryltrione or agriculturally
acceptable salt thereof is applied to vegetation or an area
adjacent the vegetation or applied to soil or water to prevent the
emergence or growth of vegetation in an amount of 1-200 g ai/ha
(e.g., 1-175 g ai/ha, 1-150 g ai/ha, 1-100 g ai/ha, 1-75 g ai/ha,
1-50 g ai/ha, 1-25 g ai/ha, 1-15 g ai/ha, 1-10 g ai/ha, 5-20 g
ai/ha, 10-30 g ai/ha, 20-40 g ai/ha, 30-50 g ai/ha, 40-60 g ai/ha,
50-70 g ai/ha, 60-80 g ai/ha, 70-90 g ai/ha, 80-100 g ai/ha, 90-110
g ai/ha, 100-120 g ai/ha, 110-130 g ai/ha, 120-140 g ai/ha, or
130-150 g ai/ha).
[0375] Topramezone
[0376] Topramezone, shown below, is
[3-(4,5-dihydro-3-isoxazolyl)-2-methyl-4-(methylsulfonyl)phenyl](5-hydrox-
y-1-methyl-1H-pyrazol-4-yl)methanone. Its herbicidal activity is
exemplified in The Pesticide Manual. Exemplary uses of topramezone
include its use for post-emergence weed control in maize.
##STR00049##
[0377] In some embodiments, topramezone can be provided as an
agriculturally acceptable salt of topramezone.
[0378] The topramezone or agriculturally acceptable salt thereof
can be applied to vegetation or an area adjacent the vegetation or
applied to soil or water to prevent the emergence or growth of
vegetation in an amount sufficient to induce a herbicidal effect.
In some embodiments, the topramezone or agriculturally acceptable
salt thereof is applied to vegetation or an area adjacent the
vegetation or applied to soil or water to prevent the emergence or
growth of vegetation in an amount of 1 g ai/ha or more (e.g., 2 g
ai/ha or more, 4 g ai/ha or more, 6 g ai/ha or more, 8 g ai/ha or
more, 10 g ai/ha or more, 15 g ai/ha or more, 20 g ai/ha or more,
25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g
ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha
or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or
more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more,
90 g ai/ha or more, 95 g ai/ha or more, or 100 g ai/ha or
more).
[0379] In some embodiments, the topramezone or agriculturally
acceptable salt thereof is applied to vegetation or an area
adjacent the vegetation or applied to soil or water to prevent the
emergence or growth of vegetation in an amount of 100 g ai/ha or
less (e.g., 95 g ai/ha or less, 90 g ai/ha or less, 85 g ai/ha or
less, 80 g ai/ha or less, 75 g ai/ha or less, 70 g ai/ha or less,
65 g ai/ha or less, 60 g ai/ha or less, 55 g ai/ha or less, 50 g
ai/ha or less, 45 g ai/ha or less, 40 g ai/ha or less, 35 g ai/ha
or less, 30 g ai/ha or less, 25 g ai/ha or less, 20 g ai/ha or
less, 15 g ai/ha or less, 10 g ai/ha or less, 9 g ai/ha or less, 8
g ai/ha or less, 7 g ai/ha or less, 6 g ai/ha or less, 5 g ai/ha or
less, 4.5 g ai/ha or less, 4 g ai/ha or less, 3.5 g ai/ha or less,
3 g ai/ha or less, 2.5 g ai/ha or less, 2 g ai/ha or less, 1.5 g
ai/ha or less, or 1 g ai/ha or less).
[0380] The topramezone or an agriculturally acceptable salt thereof
can be applied to vegetation or an area adjacent the vegetation or
applied to soil or water to prevent the emergence or growth of
vegetation in an amount ranging from any of the minimum values
described above to any of the maximum values described above. In
some embodiments, the topramezone or agriculturally acceptable salt
thereof is applied to vegetation or an area adjacent the vegetation
or applied to soil or water to prevent the emergence or growth of
vegetation in an amount of 1-100 g ai/ha (e.g., 1-90 g ai/ha, 1-80
g ai/ha, 1-70 g ai/ha, 1-60 g ai/ha, 1-50 g ai/ha, 1-25 g ai/ha,
1-15 g ai/ha, 1-10 g ai/ha, 5-20 g ai/ha, 10-25 g ai/ha, 15-25 g
ai/ha, 20-30 g ai/ha, 20-40 g ai/ha, 30-50 g ai/ha, 40-60 g ai/ha,
50-70 g ai/ha, 60-80 g ai/ha, 70-90 g ai/ha, 80-100 g ai/ha, or
90-100 g ai/ha).
II. Compositions
[0381] A. Herbicidal Mixtures or Combinations
[0382] The (a) pyridine carboxylic acid herbicide or an
agriculturally acceptable N-oxide, salt, or ester thereof is mixed
with or applied in combination with (b) an HPPD inhibitor or an
agriculturally acceptable salt or ester thereof (a) and (b) can be
provided in an amount sufficient to induce a herbicidal effect. In
some embodiments, (a) and (b) are used in an amount sufficient to
induce an unexpected herbicidal effect while still showing good
crop compatibility (for example their use in crops does not result
in significant increased damage to crops when compared to the
individual application of the herbicidal compounds (a) or (b)). In
some embodiments, (a) and (b) can be provided together to furnish a
herbicidal effect that is more than the additive effect of (a) and
(b) when used separately. In some embodiments, the damage or injury
to the undesired vegetation caused by the compositions and methods
disclosed herein is evaluated using a scale from 0% to 100%, when
compared with the untreated control vegetation, wherein 0%
indicates no damage to the undesired vegetation and 100% indicates
complete destruction of the undesired vegetation.
[0383] In some embodiments, the joint action of a pyridine
carboxylic acid herbicide or an agriculturally acceptable N-oxide,
salt, or ester thereof and an HPPD inhibitor or an agriculturally
acceptable salt or ester thereof results in enhanced activity
against undesired vegetation even at application rates below those
typically used for the pesticide to have a herbicidal effect on its
own. In some embodiments, the compositions and methods disclosed
herein can, based on the individual components, be used at lower
application rates to achieve a herbicidal effect comparable to the
effect produced by the individual components at normal application
rates. In some embodiments, the compositions and methods disclosed
herein provide an accelerated action on undesired vegetation (such
as they may effect damaging of undesired vegetation more quickly
compared with application of the individual herbicides).
[0384] In some embodiments, the observed effect for undesired
vegetation is at least 1%, at least 2%, at least 3%, at least 4%,
at least 5%, at least 10%, at least 15%, at least 20%, or at least
25% greater than the effect (E) calculated according to the Colby
method (e.g., an observed effect of 96% would be 4% greater than an
calculated effect (E) of 92%). In some embodiments, for undesired
vegetation, the difference (D.sub.O) between 100% and the observed
effect is at least 5%, at least 10%, at least 15%, at least 20%, at
least 25%, at least 30%, at least 35%, at least 40%, at least 45%,
or at least 50% less than the difference (D.sub.E) between 100% and
the effect (E) calculated according to the Colby equation (e.g., an
observed effect of 96% would produce a D.sub.O of 4%, a calculated
effect (E) of 92% would produce a D.sub.E of 8%, and D.sub.O would
be 50% less than or half of D.sub.E).
[0385] In some embodiments, the weight ratio of (a) a pyridine
carboxylic acid herbicide or an agriculturally acceptable N-oxide,
salt, or ester thereof (in g ae/ha) to (b) an HPPD inhibitor or an
agriculturally acceptable salt or ester thereof (in g ai/ha) is
1:8000 or more (e.g., 1:7000 or more, 1:6000 or more, 1:5000 or
more, 1:4000 or more, 1:3000 or more, 1:2000 or more, 1:1800 or
more, 1:1600 or more, 1:1400 or more, 1:1200 or more, 1:1000 or
more, 1:900 or more, 1:800 or more, 1:700 or more, 1:600 or more,
1:500 or more, 1:400 or more, 1:300 or more, 1:200 or more, 1:100
or more, 1:90 or more, 1:80 or more, 1:70 or more, 1:60 or more,
1:50 or more, 1:40 or more, 1:30 or more, 1:20 or more, 1:10 or
more, 1:9 or more, 1:8 or more, 1:7 or more, 1:6 or more, 1:5 or
more, 1:4 or more, 1:3 or more, 1:2 or more, 1:1.9 or more, 1:1.8
or more, 1:1.7 or more, 1:1.6 or more, 1:1.5 or more, 1:1.4 or
more, 1:1.3 or more, 1:1.2 or more, 1:1.1 or more, 1:1 or more,
1.1:1 or more, 1.2:1 or more, 1.3:1 or more, 1.4:1 or more, 1.5:1
or more, 1.6:1 or more, 1.7:1 or more, 1.8:1 or more, 1.9:1 or
more, 2:1 or more, 3:1 or more, 4:1 or more, 5:1 or more, 6:1 or
more, 7:1 or more, 8:1 or more, 9:1 or more, 10:1 or more, 20:1 or
more, 30:1 or more, 40:1 or more, 50:1 or more, 60:1 or more, 70:1
or more, 80:1 or more, 90:1 or more, 100:1 or more, 200:1 or more,
300:1 or more, 400:1 or more, 500:1 or more, 600:1 or more, 700:1
or more, 800:1 or more, 900:1 or more, or 1000:1 or more).
[0386] In some embodiments, the weight ratio of (a) a pyridine
carboxylic acid herbicide or an agriculturally acceptable N-oxide,
salt, or ester thereof (in g ae/ha) to (b) an HPPD inhibitor or an
agriculturally acceptable salt or ester thereof (in g ai/ha) is
1000:1 or less (e.g., 900:1 or less, 800:1 or less, 700:1 or less,
600:1 or less, 500:1 or less, 400:1 or less, 300:1 or less, 250:1
or less, 200:1 or less, 100:1 or less, 90:1 or less, 80:1 or less,
70:1 or less, 60:1 or less, 50:1 or less, 40:1 or less, 30:1 or
less, 20:1 or less, 15:1 or less, 10:1 or less, 9:1 or less, 8:1 or
less, 7:1 or less, 6:1 or less, 5:1 or less, 4:1 or less, 3:1 or
less, 2:1 or less, 1.9:1 or less, 1.8:1 or less, 1.7:1 or less,
1.6:1 or less, 1.5:1 or less, 1.4:1 or less, 1.3:1 or less, 1.2:1
or less, 1.1:1 or less, 1:1 or less, 1:1.1 or less, 1:1.2 or less,
1:1.3 or less, 1:1.4 or less, 1:1.5 or less, 1:1.6 or less, 1:1.7
or less, 1:1.8 or less, 1:1.9 or less, 1:2 or less, 1:3 or less,
1:4 or less, 1:5 or less, 1:6 or less, 1:7 or less, 1:8 or less,
1:9 or less, 1:10 or less, 1:20 or less, 1:30 or less, 1:40 or
less, 1:50 or less, 1:60 or less, 1:70 or less, 1:80 or less, 1:90
or less, 1:100 or less, 1:200 or less, 1:300 or less, 1:400 or
less, 1:500 or less, 1:600 or less, 1:700 or less, 1:800 or less,
1:900 or less, 1:1000 or less, 1:1200 or less, 1:1400 or less,
1:1600 or less, 1:1800 or less, 1:2000 or less, 1:3000 or less,
1:4000 or less, 1:5000 or less, 1:6000 or less, 1:7000 or less, or
1:8000 or less).
[0387] The weight ratio of (a) a pyridine carboxylic acid herbicide
or an agriculturally acceptable N-oxide, salt, or ester thereof (in
g ae/ha) to (b) an HPPD inhibitor or an agriculturally acceptable
salt or ester thereof (in g ai/ha) can range from any of the
minimum ratios described above to any of the maximum values
described above. In some embodiments, the weight ratio of (a) a
pyridine carboxylic acid herbicide or an agriculturally acceptable
N-oxide, salt, or ester thereof (in g ae/ha) to (b) an HPPD
inhibitor or an agriculturally acceptable salt or ester thereof (in
g ai/ha) is from 1:8000 to 1000:1 (e.g., from 1:6000 to 1000:1,
from 1:5000 to 1000:1, from 1:4000 to 800:1, from 1:3000 to 600:1,
from 1:2500 to 400:1, from 1:2000 to 250:1, from 1:1000 to 125:1,
1:800 to 100:1, from 1:500 to 60:1, from 1:400 to 200:1, from 1:200
to 100:1, from 1:125 to 15:1, from 1:100 to 100:1, from 1:50 to
50:1, from 1:40 to 40:1, from 1:30 to 30:1, from 1:20 to 20:1, from
1:10 to 10:1, 1:1000 to 20:1, from 1:900 to 10:1, from 1:900 to
50:1, from 1:800 to 40:1, from 1:700 to 30:1, from 1:600 to 20:1,
from 1:500 to 15:1, from 1:400 to 10:1, from 1:300 to 9:1, from
1:200 to 8:1, from 1:100 to 7:1, from 1:50 to 6:1, from 1:40 to
5:1, from 1:30 to 5:1, from 1:30 to 4:1, from 1:20 to 3:1, from
1:10 to 2:1, from 1:5 to 5:1, from 1:4 to 4:1, from 1:3 to 3:1, or
from 1:2 to 2:1).
[0388] In some embodiments, the active ingredients in the
compositions disclosed herein consist of (a) a pyridine carboxylic
acid herbicide or an agriculturally acceptable N-oxide, salt, or
ester thereof and (b) an HPPD inhibitor or an agriculturally
acceptable salt or ester thereof.
[0389] B. Formulations
[0390] The present disclosure also relates to formulations of the
compositions and methods disclosed herein. In some embodiments, the
formulation can be in the form of a single package formulation
including both (a) a pyridine carboxylic acid herbicide or an
agriculturally acceptable N-oxide, salt, or ester thereof, and (b)
an HPPD inhibitor or an agriculturally acceptable salt or ester
thereof. In some embodiments, the formulation can be in the form of
a single package formulation including both (a) and (b) and further
including at least one additive. In some embodiments, the
formulation can be in the form of a two-package formulation,
wherein one package contains (a) and optionally at least one
additive while the other package contains (b) and optionally at
least one additive. In some embodiments of the two-package
formulation, the formulation including (a) and optionally at least
one additive and the formulation including (b) and optionally at
least one additive are mixed before application and then applied
simultaneously. In some embodiments, the mixing is performed as a
tank mix (e.g., the formulations are mixed immediately before or
upon dilution with water). In some embodiments, the formulation
including (a) and the formulation including (b) are not mixed but
are applied sequentially (in succession), for example, immediately
or within 1 hour, within 2 hours, within 4 hours, within 8 hours,
within 16 hours, within 24 hours, within 2 days, or within 3 days,
of each other.
[0391] In some embodiments, the formulation of (a) and (b) is
present in suspended, emulsified, or dissolved form. Exemplary
formulations include, but are not limited to, aqueous solutions,
powders, suspensions, also highly-concentrated aqueous, oily or
other suspensions or dispersions, aqueous emulsions, aqueous
microemulsions, aqueous suspo-emulsions, oil dispersions,
self-emulsifying formulations, pastes, dusts, and materials for
spreading or granules.
[0392] In some embodiments, (a) a pyridine carboxylic acid
herbicide or an agriculturally acceptable N-oxide, salt, or ester
thereof and/or (b) an HPPD inhibitor or an agriculturally
acceptable salt or ester thereof is an aqueous solution that can be
diluted before use. In some embodiments, (a) and/or (b) is provided
as a high-strength formulation such as a concentrate. In some
embodiments, the concentrate is stable and retains potency during
storage and shipping. In some embodiments, the concentrate is a
clear, homogeneous liquid that is stable at temperatures of
54.degree. C. or greater. In some embodiments, the concentrate does
not exhibit any precipitation of solids at temperatures of
-10.degree. C. or higher. In some embodiments, the concentrate does
not exhibit separation, precipitation, or crystallization of any
components at low temperatures. For example, the concentrate
remains a clear solution at temperatures below 0.degree. C. (e.g.,
below -5.degree. C., below -10.degree. C., below -15.degree. C.).
In some embodiments, the concentrate exhibits a viscosity of less
than 50 centipoise (50 megapascals), even at temperatures as low as
5.degree. C.
[0393] The compositions and methods disclosed herein can also be
mixed with or applied with an additive. In some embodiments, the
additive can be diluted in water or can be concentrated. In some
embodiments, the additive is added sequentially. In some
embodiments, the additive is added simultaneously. In some
embodiments, the additive is premixed with the pyridine carboxylic
acid herbicide or agriculturally acceptable N-oxide, salt, or ester
thereof. In some embodiments, the additive is premixed with the
HPPD inhibitor or agriculturally acceptable salt or ester
thereof.
[0394] C. Other Actives
[0395] In some embodiments, the additive is an additional
pesticide. For example, the compositions described herein can be
applied in conjunction with one or more additional herbicides to
control undesirable vegetation. The composition can be formulated
with the one or more additional herbicides, tank mixed with the one
or more additional herbicides, or applied sequentially with the one
or more additional herbicides. Exemplary additional herbicides
include, but are not limited to: 4-CPA, 4-CPB, 4-CPP, 2,4-D, 2,4-D
choline salt, 2,4-D esters and amines, 2,4-DB, 3,4-DA, 3,4-DB,
2,4-DEB, 2,4-DEP, 3,4-DP, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, acetochlor,
acifluorfen, aclonifen, acrolein, alachlor, allidochlor, alloxydim,
allyl alcohol, alorac, ametridione, ametryn, amibuzin,
amicarbazone, aminocyclopyrachlor, 4-aminopicolinic acid based
herbicides, such as halauxifen, halauxifen-methyl,
4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridin-
ecarboxylic acid, benzyl
4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridin-
ecarboxylate, and those described in U.S. Pat. Nos. 7,314,849 and
7,432,227 to Balko, et al., aminopyralid, amiprofos-methyl,
amitrole, ammonium sulfamate, anilofos, anisuron, asulam, atraton,
atrazine, azafenidin, aziprotryne, barban, BCPC, beflubutamid,
benazolin, bencarbazone, benfluralin, benfuresate, bensulide,
benthiocarb, bentazon-sodium, benzadox, benzfendizone, benzipram,
benzobicyclon, benzofenap, benzofluor, benzoylprop, benzthiazuron,
bicyclopyrone, bifenox, bilanafos, borax, bromacil, bromobonil,
bromobutide, bromofenoxim, bromoxynil, brompyrazon, butachlor,
butafenacil, butamifos, butenachlor, buthidazole, buthiuron,
butralin, butroxydim, buturon, butylate, cacodylic acid,
cafenstrole, calcium chlorate, calcium cyanamide, cambendichlor,
carbasulam, carbetamide, carboxazole, chlorprocarb,
carfentrazone-ethyl, CDEA, CEPC, chlomethoxyfen, chloramben,
chloranocryl, chlorazifop, chlorazine, chlorbromuron, chlorbufam,
chloreturon, chlorfenac, chlorfenprop, chlorflurazole,
chlorflurenol, chloridazon, chlornitrofen, chloropon,
chlorotoluron, chloroxuron, chloroxynil, chlorpropham, chlorthal,
chlorthiamid, cinidon-ethyl, cinmethylin, cisanilide, clacyfos,
clethodim, cliodinate, clodinafop-propargyl, clofop, clomazone,
clomeprop, cloprop, cloproxydim, clopyralid, CMA, copper sulfate,
CPMF, CPPC, credazine, cresol, cumyluron, cyanatryn, cyanazine,
cycloate, cycloxydim, cycluron, cyhalofop-butyl, cyperquat,
cyprazine, cyprazole, cypromid, daimuron, dalapon, dazomet,
delachlor, desmedipham, desmetryn, di-allate, dicamba, dichlobenil,
dichloralurea, dichlormate, dichlorprop, dichlorprop-P,
diclofop-methyl, diethamquat, diethatyl, difenopenten, difenoxuron,
difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate,
dimethachlor, dimethametryn, dimethenamid, dimethenamid-P,
dimexano, dimidazon, dinitramine, dinofenate, dinoprop, dinosam,
dinoseb, dinoterb, diphenamid, dipropetryn, diquat, disul,
dithiopyr, diuron, DMPA, DNOC, DSMA, EBEP, eglinazine, endothal,
epronaz, EPTC, erbon, esprocarb, ethalfluralin, ethbenzamide,
ethidimuron, ethiolate, ethobenzamid, etobenzamid, ethofumesate,
ethoxyfen, etinofen, etnipromid, etobenzanid, EXD, fenasulam,
fenoprop, fenoxaprop, fenoxaprop-P-ethyl,
fenoxaprop-P-ethyl+isoxadifen-ethyl, fenoxasulfone, fenquinotrione,
fenteracol, fenthiaprop, fentrazamide, fenuron, ferrous sulfate,
flamprop, flamprop-M, fluazifop, fluazifop-P-butyl, fluazolate,
fluchloralin, flufenacet, flufenican, flufenpyr-ethyl, flumezin,
flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron,
fluorodifen, fluoroglycofen, fluoromidine, fluoronitrofen,
fluothiuron, flupoxam, flupropacil, flupropanate, fluridone,
flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone,
fluthiacet, fomesafen, fosamine, fumiclorac, furyloxyfen,
glufosinate, glufosinate-ammonium, glufosinate-P-ammonium,
glyphosate salts and esters, halosafen, haloxydine,
hexachloroacetone, hexaflurate, hexazinone, indanofan, indaziflam,
iodobonil, iodomethane, ioxynil, ipazine, ipfencarbazone,
iprymidam, isocarbamid, isocil, isomethiozin, isonoruron,
isopolinate, isopropalin, isoproturon, isouron, isoxaben,
isoxachlortole, isoxaflutole, isoxapyrifop, karbutilate,
ketospiradox, lactofen, lenacil, linuron, MAA, MAMA, MCPA esters
and amines, MCPA-thioethyl, MCPB, mecoprop, mecoprop-P, medinoterb,
mefenacet, mefluidide, mesoprazine, mesotrione, metam, metamifop,
metamitron, metazachlor, metflurazon, methabenzthiazuron,
methalpropalin, methazole, methiobencarb, methiozolin, methiuron,
methometon, methoprotryne, methyl bromide, methyl isothiocyanate,
methyldymron, metobenzuron, metobromuron, metolachlor, metoxuron,
metribuzin, molinate, monalide, monisouron, monochloroacetic acid,
monolinuron, monuron, morfamquat, MSMA, naproanilide, napropamide,
napropamide-M, naptalam, neburon, nipyraclofen, nitralin, nitrofen,
nitrofluorfen, norflurazon, noruron, OCH, orbencarb,
ortho-dichlorobenzene, oryzalin, oxadiargyl, oxadiazon, oxapyrazon,
oxaziclomefone, oxyfluorfen, paraflufen-ethyl, parafluron,
paraquat, pebulate, pelargonic acid, pendimethalin,
pentachlorophenol, pentanochlor, pentoxazone, perfluidone,
pethoxamid, phenisopham, phenmedipham, phenmedipham-ethyl,
phenobenzuron, phenylmercury acetate, picloram, picolinafen,
pinoxaden, piperophos, potassium arsenite, potassium azide,
potassium cyanate, pretilachlor, procyazine, prodiamine,
profluazol, profluralin, profoxydim, proglinazine,
prohexadione-calcium, prometon, prometryn, pronamide, propachlor,
propanil, propaquizafop, propazine, propham, propisochlor,
propyzamide, prosulfalin, prosulfocarb, proxan, prynachlor,
pydanon, pyraclonil, pyraflufen-ethyl, pyrasulfotole, pyrazogyl,
pyrazolynate, pyrazoxyfen, pyributicarb, pyriclor, pyridafol,
pyridate, quinclorac, quinmerac, quinoclamine, quinonamid,
quizalofop, quizalofop-P-ethyl, rhodethanil, saflufenacil,
S-metolachlor, sebuthylazine, secbumeton, sethoxydim, siduron,
simazine, simeton, simetryn, SMA, sodium arsenite, sodium azide,
sodium chlorate, sulcotrione, sulfallate, sulfentrazone, sulfosate,
sulfuric acid, sulglycapin, swep, TCA, tebutam, tebuthiuron,
tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb,
terbuchlor, terbumeton, terbuthylazine, terbutryn, tetrafluron,
thenylchlor, thiameturon, thiazafluron, thiazopyr, thidiazimin,
thidiazuron, thiobencarb, tiafenacil, tiocarbazil, tioclorim,
tolpyralate, topramezone, tralkoxydim, tri-allate, triafamone,
triaziflam, tricamba, triclopyr choline salt, triclopyr esters and
amines, tridiphane, trietazine, trifluralin, trifop, trifopsime,
trihydroxytriazine, trimeturon, tripropindan, tritac, vernolate,
xylachlor and salts, esters, optically active isomers, and mixtures
thereof.
[0396] In some embodiments, the additional pesticide or an
agriculturally acceptable salt or ester thereof is provided in a
premixed formulation with (a), (b), or combinations thereof. In
some embodiments, the pyridine carboxylic acid herbicide or an
agriculturally acceptable N-oxide, salt, or ester thereof is
provided in a premixed formulation with an additional pesticide. In
some embodiments, the HPPD inhibitor or an agriculturally
acceptable salt or ester thereof is provided in a premixed
formulation with an additional pesticide. In some embodiments, the
benzobicyclon, the benzofenap, the bicyclopyrone, the
fenquinotrione, the isoxachlortole, the isoxaflutole, the
mesotrione, the pyrasulfotole, the pyrazolynate, the pyrazoxyfen,
the sulcotrione, the tembotrione, the tefuryltrione, or the
topramezone, or an agriculturally acceptable salt or ester thereof,
is provided in a premixed formulation with an additional
pesticide.
[0397] D. Adjuvants/Carriers/Colorants/Adhesives
[0398] In some embodiments, the additive includes an agriculturally
acceptable adjuvant. Exemplary agriculturally acceptable adjuvants
include, but are not limited to, antifreeze agents, antifoam
agents, compatibilizing agents, sequestering agents, neutralizing
agents and buffers, corrosion inhibitors, colorants, odorants,
penetration aids, wetting agents, spreading agents, dispersing
agents, thickening agents, freeze point depressants, antimicrobial
agents, crop oil, safeners, adhesives (for instance, for use in
seed formulations), surfactants, protective colloids, emulsifiers,
tackifiers, and mixtures thereof.
[0399] Exemplary agriculturally acceptable adjuvants include, but
are not limited to, crop oil concentrate (mineral oil
(85%)+emulsifiers (15%)) or less, nonylphenol ethoxylate or less,
benzylcocoalkyldimethyl quaternary ammonium salt or less, blend of
petroleum hydrocarbon, alkyl esters, organic acid, and anionic
surfactant or less, C.sub.9-C.sub.11 alkylpolyglycoside or less,
phosphate alcohol ethoxylate or less, natural primary alcohol
(C.sub.12-C.sub.16) ethoxylate or less, di-sec-butylphenol EO-PO
block copolymer or less, polysiloxane-methyl cap or less,
nonylphenol ethoxylate+urea ammonium nitrate or less, emulsified
methylated seed oil or less, tridecyl alcohol (synthetic)
ethoxylate (8 EO) or less, tallow amine ethoxylate (15 EO) or less,
and PEG(400) dioleate-99.
[0400] In some embodiments, the additive is a safener, which is an
organic compound leading to better crop plant compatibility when
applied with a herbicide. In some embodiments, the safener itself
is herbicidally active. In some embodiments, the safener acts as an
antidote or antagonist in the crop plants and can reduce or prevent
damage to the crop plants. Exemplary safeners include, but are not
limited to, AD-67 (MON 4660), benoxacor, benthiocarb, brassinolide,
cloquintocet (mexyl), cyometrinil, cyprosulfamide, daimuron,
dichlormid, dicyclonon, dietholate, dimepiperate, disulfoton,
fenchlorazole, fenchlorazole-ethyl, fenclorim, flurazole,
fluxofenim, furilazole, harpin proteins, isoxadifen-ethyl,
jiecaowan, jiecaoxi, mefenpyr, mefenpyr-diethyl, mephenate,
naphthalic anhydride,
2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine,
4-(dichloroacetyl)-1-oxa-4-azaspiro [4.5]decane, oxabetrinil,
R29148, and N-phenyl-sulfonylbenzoic acid amides, as well as
thereof agriculturally acceptable salts and, provided they have a
carboxyl group, their agriculturally acceptable derivatives. In
some embodiments, the safener can be cloquintocet or an ester or
salt or ester thereof, such as cloquintocet (mexyl). In some
embodiments, the safener can be dichlormid. In some embodiments,
the safener is employed in rice, cereal, corn, or maize. For
example, dichlormid or cloquintocet can be used to antagonize
harmful effects of the compositions on rice, row crops, and
cereals.
[0401] Exemplary surfactants (e.g., wetting agents, tackifiers,
dispersants, emulsifiers) include, but are not limited to, the
alkali metal salts, alkaline earth metal salts and ammonium salts
of aromatic sulfonic acids, for example lignosulfonic acids,
phenolsulfonic acids, naphthalenesulfonic acids, and
dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl- and
alkylarylsulfonates, alkyl sulfates, lauryl ether sulfates and
fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and
octadecanols, and also of fatty alcohol glycol ethers, condensates
of sulfonated naphthalene and its derivatives with formaldehyde,
condensates of naphthalene or of the naphthalene sulfonic acids
with phenol and formaldehyde, polyoxyethylene octylphenol ether,
ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl or
tributylphenyl polyglycol ether, alkyl aryl polyether alcohols,
isotridecyl alcohol, fatty alcohol/ethylene oxide condensates,
ethoxylated castor oil, polyoxyethylene alkyl ethers or
polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether
acetate, sorbitol esters, lignosulfite waste liquors and proteins,
denatured proteins, polysaccharides (e.g., methylcellulose),
hydrophobically modified starches, polyvinyl alcohol,
polycarboxylates, polyalkoxylates, polyvinyl amine,
polyethyleneimine, polyvinylpyrrolidone and copolymers thereof.
[0402] Exemplary thickeners include, but are not limited to,
polysaccharides, such as xanthan gum, and organic and inorganic
sheet minerals, and mixtures thereof.
[0403] Exemplary antifoam agents include, but are not limited to,
silicone emulsions, long-chain alcohols, fatty acids, salts of
fatty acids, organofluorine compounds, and mixtures thereof.
[0404] Exemplary antimicrobial agents include, but are not limited
to, bactericides based on dichlorophen and benzyl alcohol
hemiformal, and isothiazolinone derivates, such as
alkylisothiazolinones and benzisothiazolinones, and mixtures
thereof.
[0405] Exemplary antifreeze agents, include, but are not limited to
ethylene glycol, propylene glycol, urea, glycerol, and mixtures
thereof.
[0406] Exemplary colorants include, but are not limited to, the
dyes known under the names Rhodamine B, pigment blue 15:4, pigment
blue 15:3, pigment blue 15:2, pigment blue 15:1, pigment blue 80,
pigment yellow 1, pigment yellow 13, pigment red 112, pigment red
48:2, pigment red 48:1, pigment red 57:1, pigment red 53:1, pigment
orange 43, pigment orange 34, pigment orange 5, pigment green 36,
pigment green 7, pigment white 6, pigment brown 25, basic violet
10, basic violet 49, acid red 51, acid red 52, acid red 14, acid
blue 9, acid yellow 23, basic red 10, basic red 108, and mixtures
thereof.
[0407] Exemplary adhesives include, but are not limited to,
polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, tylose,
and mixtures thereof.
[0408] In some embodiments, the additive includes a carrier. In
some embodiments, the additive includes a liquid or solid carrier.
In some embodiments, the additive includes an organic or inorganic
carrier. Exemplary liquid carriers include, but are not limited to,
petroleum fractions or hydrocarbons such as mineral oil, aromatic
solvents, paraffinic oils, and the like or less, vegetable oils
such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower
seed oil, coconut oil, corn oil, cottonseed oil, linseed oil, palm
oil, peanut oil, safflower oil, sesame oil, tung oil and the like
or less, esters of the above vegetable oils or less, esters of
monoalcohols or dihydric, trihydric, or other lower polyalcohols
(4-6 hydroxy containing), such as 2-ethyl hexyl stearate, n-butyl
oleate, isopropyl myristate, propylene glycol dioleate, di-octyl
succinate, di-butyl adipate, di-octyl phthalate and the like or
less, esters of mono, di and polycarboxylic acids and the like,
toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl
ketone, cyclohexanone, trichloroethylene, perchloroethylene, ethyl
acetate, amyl acetate, butyl acetate, propylene glycol monomethyl
ether and diethylene glycol monomethyl ether, methyl alcohol, ethyl
alcohol, isopropyl alcohol, amyl alcohol, ethylene glycol,
propylene glycol, glycerine, N-methyl-2-pyrrolidinone, N,N-dimethyl
alkylamides, dimethyl sulfoxide, liquid fertilizers and the like,
and water as well as mixtures thereof. Exemplary solid carriers
include, but are not limited to, silicas, silica gels, silicates,
talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite,
diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium
oxide, ground synthetic materials, pyrophyllite clay, attapulgus
clay, kieselguhr, calcium carbonate, bentonite clay, Fuller's
earth, cottonseed hulls, wheat flour, soybean flour, pumice, wood
flour, walnut shell flour, lignin, ammonium sulfate, ammonium
phosphate, ammonium nitrate, ureas, cereal meal, tree bark meal,
wood meal and nutshell meal, cellulose powders, and mixtures
thereof.
[0409] In some embodiments, emulsions, pastes or oil dispersions
can be prepared by homogenizing (a) and (b) in water by means of
wetting agent, tackifier, dispersant or emulsifier. In some
embodiments, concentrates suitable for dilution with water are
prepared, containing (a), (b), a wetting agent, a tackifier, and a
dispersant or emulsifier.
[0410] In some embodiments, powders or materials for spreading and
dusts can be prepared by mixing or concomitant grinding of (a) and
(b) and optionally a safener with a solid carrier.
[0411] In some embodiments, granules (e.g., coated granules,
impregnated granules and homogeneous granules) can be prepared by
binding the (a) and (b) to solid carriers.
[0412] The formulations disclosed herein provide a herbicidally
effective amount of (a) and (b). In some embodiments, the
concentrations of (a) and (b) in the formulations can be varied. In
some embodiments, the formulations contain from 1% to 95% (e.g.,
from 5% to 95%, from 10% to 80%, from 20% to 70%, from 30% to 50%)
by total weight of (a) and (b). In formulations designed to be
employed as concentrates, (a) and (b) can be present in a
concentration of from 0.1 to 98 weight percent (0.5 to 90 weight
percent), based on the total weight of the formulation.
Concentrates can be diluted with an inert carrier, such as water,
prior to application. The diluted formulations applied to undesired
vegetation or the locus of undesired vegetation can contain from
0.0006 to 8.0 weight percent of (a) and (b) (e.g., from 0.001 to
5.0 weight percent), based on the total weight of the diluted
formulation.
[0413] In some embodiments, (a) and (b), independently, can be
employed in a purity of from 90% to 100% (e.g., from 95% to 100%)
according to nuclear magnetic resonance (NMR) spectrometry. In some
embodiments, the concentrations of (a), (b), and additional
pesticides in the formulations can be varied. In some embodiments,
the formulations contain from 1% to 95% (e.g., from 5% to 95%, from
10% to 80%, from 20% to 70%, from 30% to 50%) by total weight of
(a), (b), and additional pesticides. In some embodiments, (a), (b),
and additional pesticides, independently, can be employed in a
purity of from 90% to 100% (e.g., from 95% to 100%) according to
NMR spectrometry.
III. Methods of Use
[0414] A. Methods of Application
[0415] The compositions disclosed herein can be applied in any
known technique for applying herbicides. Exemplary application
techniques include, but are not limited to, spraying, atomizing,
dusting, spreading, or direct application into water (in-water).
The method of application can vary depending on the intended
purpose. In some embodiments, the method of application can be
chosen to ensure the finest possible distribution of the
compositions disclosed herein.
[0416] In some embodiments, a method of controlling undesirable
vegetation which includes contacting the vegetation or the locus
thereof with or applying to the soil or water to prevent the
emergence or growth of vegetation any of the compositions is
disclosed herein.
[0417] The compositions disclosed herein can be applied
pre-emergence (before the emergence of undesirable vegetation) or
post-emergence (during and/or after emergence of the undesirable
vegetation). If desired, the compositions can be applied as an
in-water application. In some embodiments, the pyridine carboxylic
acid herbicide or or an agriculturally acceptable N-oxide, salt, or
ester thereof and the HPPD inhibitor are applied simultaneously. In
some embodiments, (a) and (b) can be provided together to furnish a
herbicidal effect that is more than the additive effect of (a) and
(b) when used separately.
[0418] When the compositions are used in crops, the compositions
can be applied after seeding and before or after the emergence of
the crop plants. In some embodiments, the compositions disclosed
herein show good crop tolerance even when the crop has already
emerged and can be applied during or after the emergence of the
crop plants. In some embodiments, when the compositions are used in
crops, the compositions can be applied before seeding of the crop
plants.
[0419] In some embodiments, the compositions disclosed herein are
applied to vegetation or an area adjacent the vegetation or applied
to soil or water to prevent the emergence or growth of vegetation
by spraying (e.g., foliar spraying). In some embodiments, the
spraying techniques use, for example, water as carrier and spray
liquor rates of from 10 liters per hectare (L/ha) to 2000 L/ha
(e.g., from 50 L/ha to 1000 L/ha or from 100 to 500 L/ha). In some
embodiments, the compositions disclosed herein are applied by the
low-volume or the ultra-low-volume method. In some embodiments,
wherein the compositions disclosed herein are less well tolerated
by certain crop plants, the compositions can be applied with the
aid of the spray apparatus in such a way that they come into little
contact, if any, with the leaves of the sensitive crop plants while
reaching the leaves of undesirable vegetation that grows underneath
or the bare soil (e.g., post-directed or lay-by). In some
embodiments, the compositions disclosed herein can be applied as
dry formulations (e.g., granules, WDGs, etc.) into water.
[0420] In some embodiments, herbicidal activity is exhibited by the
compounds of the mixture when they are applied directly to the
plant or to the locus of the plant at any stage of growth or before
planting or emergence. The effect observed can depend upon the type
of undesirable vegetation to be controlled, the stage of growth of
the undesirable vegetation, the application parameters of dilution
and spray drop size, the particle size of solid components, the
environmental conditions at the time of use, the specific compound
employed, the specific adjuvants and carriers employed, the soil
type, and the like, as well as the amount of chemical applied. In
some embodiments, these and other factors can be adjusted to
promote non-selective or selective herbicidal action. In some
cases, the compositions are applied to relatively immature
undesirable vegetation.
[0421] The compositions and methods disclosed herein can be used to
control undesired vegetation in a variety of crop and non-crop
applications. In some embodiments, the compositions and methods
disclosed herein can be used for controlling undesired vegetation
in crops. Exemplary crops include, but are not limited to, wheat,
barley, triticale, rye, teff, oats, maize, cotton, soybeans,
sorghum, millet, rice, sugarcane and range land (e.g., pasture
grasses). In some embodiments, the undesirable vegetation is
controlled in a row crop (e.g., maize, sorghum, soybean, cotton, or
oilseed rape/canola). In some embodiments, the compositions and
methods disclosed herein can be used for controlling undesired
vegetation in wheat, barley, oats, rye, triticale, maize, sorgum,
millet, or genetically modified wheat, barley, maize or oats.
[0422] The compositions and methods disclosed herein can be used
for controlling undesired vegetation in non-crop areas. Exemplary
non-crop areas include, but are not limited to, turfgrass,
pastures, grasslands, fallow land, rights-of-way, aquatic settings,
tree and vine, wildlife management areas, or rangeland. In some
embodiments, the compositions and methods disclosed herein can be
used in industrial vegetation management (IVM) or for utility,
pipeline, roadside, and railroad rights-of-way applications. In
some embodiments, the compositions and methods disclosed herein can
also be used in forestry (e.g., for site preparation or for
combating undesirable vegetation in plantation forests). In some
embodiments, the compositions and methods disclosed herein can be
used to control undesirable vegetation in conservation reserve
program lands (CRP), trees, vines, grasslands, and grasses grown
for seeds. In some embodiments, the compositions and methods
disclosed herein can be used on lawns (e.g., residential,
industrial, and institutional), golf courses, parks, cemeteries,
athletic fields, and sod farms.
[0423] The compositions and methods disclosed herein can also be
used in crop plants that are resistant to, for instance,
herbicides, pathogens, and/or insects. In some embodiments, the
compositions and methods disclosed herein can be used in crop
plants that are resistant to one or more herbicides because of
genetic engineering or breeding. In some embodiments, the
compositions and methods disclosed herein can be used in crop
plants that are resistant to one or more pathogens such as plant
pathogenous fungi owing to genetic engineering or breeding. In some
embodiments, the compositions and methods disclosed herein can be
used in crop plants that are resistant to attack by insects owing
to genetic engineering or breeding. Exemplary resistant crops
include, but are not limited to, crops that are resistant to
photosystem II inhibitors, or crop plants that, owing to
introduction of the gene for Bacillus thuringiensis (or Bt) toxin
by genetic modification, are resistant to attack by certain
insects. In some embodiments, the compositions and methods
described herein also can be used in conjunction with glyphosate,
glufosinate, dicamba, phenoxy auxins, pyridyloxy auxins,
aryloxyphenoxypropionates, acetyl CoA carboxylase (ACCase)
inhibitors, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors,
protoporphyrinogen oxidase (PPO) inhibitors, triazines, and
bromoxynil to control vegetation in crops tolerant to glyphosate,
glufosinate, dicamba, phenoxy auxins, pyridyloxy auxins,
aryloxyphenoxypropionates, acetyl CoA carboxylase (ACCase)
inhibitors, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors,
protoporphyrinogen oxidase (PPO) inhibitors, triazines, bromoxynil,
or combinations thereof. In some embodiments, the undesirable
vegetation is controlled in glyphosate, glufosinate, dicamba,
phenoxy auxins, pyridyloxy auxins, aryloxyphenoxypropionates,
acetyl CoA carboxylase (ACCase) inhibitors,
4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors,
protoporphyrinogen oxidase (PPO) inhibitors, triazines, and
bromoxynil tolerant crops possessing single, multiple or stacked
traits conferring tolerance to single or multiple chemistries
and/or multiple modes of action. In some embodiments, the
undesirable vegetation can be controlled in a crop that is
ACCase-tolerant. The combination of (a), (b), and a complementary
herbicide or salt or ester thereof can be used in combination with
herbicides that are selective for the crop being treated and which
complement the spectrum of weeds controlled by these compounds at
the application rate employed. In some embodiments, the
compositions described herein and other complementary herbicides
are applied at the same time, either as a combination formulation
or as a tank mix, or as sequential applications.
[0424] The compositions and methods may be used in controlling
undesirable vegetation in crops possessing agronomic stress
tolerance (including but not limited to drought, cold, heat, salt,
water, nutrient, fertility, pH), pest tolerance (including but not
limited to insects, fungi and pathogens) and crop improvement
traits (including but not limited to yield; protein, carbohydrate,
or oil content; protein, carbohydrate, or oil composition; plant
stature and plant architecture).
[0425] In some embodiments, the compositions disclosed herein can
be used for controlling undesirable vegetation including grasses,
broadleaf weeds, sedge weeds, and combinations thereof. In some
embodiments, the compositions disclosed herein can be used for
controlling undesirable vegetation including, but not limited to,
Polygonum species such as wild buckwheat (Polygonum convolvolus),
Amaranthus species such as pigweed (Amaranthus retroflexus),
Chenopodium species such as common lambsquarters (Chenopodium album
L.), Sida species such as prickly sida (Sida spinosa L.), Ambrosia
species such as common ragweed (Ambrosia artemisiifolia), Cyperus
species such as nutsedge (Cyperus esculentus), Setaria species such
as giant foxtail (Setaria faberi), Sorghum species, Acanthospermum
species, Anthemis species, Atriplex species, Brassica species,
Cirsium species, Convolvulus species, Conyza species, such as
horseweed (Conyza canadensis), Cassia species, Commelina species,
Datura species, Euphorbia species, Geranium species, Galinsoga
species, Ipomea species such as morning-glory, Lamium species,
Malva species, Matricaria species, Persicaria species, Prosopis
species, Rumex species, Sisymbrium species, Solanum species,
Trifolium species, Xanthium species, Veronica species, Viola
species such as wild pansy (Viola tricolor), common chickweed
(Stellaria media), velvetleaf (Abutilon theophrasti), hemp sesbania
(Sesbania exaltata Cory), Anoda cristata, Bidens pilosa, Brassica
kaber, shepherd's purse (Capsella bursa-pastoris), cornflower
(Centaurea cyanus or Cyanus segetum), Galeopsis tetrahit, cleavers
Galium aparine), Helianthus annuus, Desmodium tortuosum, kochia
(Kochia scoparia), Medicago arabica, Mercurialis annua, Myosotis
arvensis, common poppy (Papaver rhoeas), Raphanus raphanistrum,
Russian thistle (Salsola kali), wild mustard (Sinapis arvensis),
Sonchus arvensis, Thlaspi arvense, Tagetes minuta, Richardia
brasiliensis, Plantago major, Plantago lanceolata, bird's-eye
speedwell (Veronica persica) and speedwell.
[0426] In certain embodiments, the undesirable vegetation includes
velvetleaf (Abutilon theophrasti, ABUTH), pigweed (Amaranthus
retrollexus, AMARE), wild oat (Avena fatua, AVEFA), winter rape
(Brassica napus, BRSNW), turnip (Brassica rapa, BRSRR), common
lambsquarters (Chenopodium album L., CHEAL), thistle (Cirsium
arvense CIRAR, barnyardgrass (Echinochloa crus-galli, ECHCG),
poinsettia (Euphorbia heterophylla, EPHHL), soybean (Glycine max,
GLXMA), sunflower (Helianthus annuus, HELAN), ivyleaf morningglory
(Ipomoea hederacea, IPOHE), kochia (Kochia scoparia, KCHSC), wild
buckwheat (Polygonum convolvulus, POLCO), giant foxtail (Setaria
faberi, SETFA), grain sorghum (Sorghum vulgare, SORVU), common
chickweed (Stellaria media, STEME), wild pansy (Viola tricolor,
VIOTR), or a combination thereof.
[0427] The herbicidal compositions described herein can be used to
control herbicide resistant or tolerant weeds. The methods
employing the compositions described herein may also be employed to
control herbicide resistant or tolerant weeds. Exemplary resistant
or tolerant weeds include, but are not limited to, biotypes
resistant or tolerant to acetolactate synthase (ALS) or
acetohydroxy acid synthase (AHAS) inhibitors (e.g., imidazolinones,
sulfonylureas, pyrimidinyl(oxy/thio)benzoates,
sulfonylaminocarbonyltriazolinones), photosystem II inhibitors
(e.g., phenylcarbamates, pyridazinones, triazines, triazinones,
uracils, amides, ureas, benzothiadiazinones, nitriles,
phenylpyridazines), acetyl CoA carboxylase (ACCase) inhibitors
(e.g., aryloxyphenoxypropionates, cyclohexanediones,
phenylpyrazolines), synthetic auxins (e.g., benzoic acids,
phenoxycarboxylic acids, pyridine carboxylic acids, quinoline
carboxylic acids), auxin transport inhibitors (e.g., phthalamates,
semicarbazones), photosystem I inhibitors (e.g., bipyridyliums),
5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors
(e.g., glyphosate), glutamine synthetase inhibitors (e.g.,
glufosinate, bialafos), microtubule assembly inhibitors (e.g.,
benzamides, benzoic acids, dinitroanilines, phosphoramidates,
pyridines), mitosis inhibitors (e.g., carbamates), very long chain
fatty acid (VLCFA) inhibitors (e.g., acetamides, chloroacetamides,
oxyacetamides, tetrazolinones), fatty acid and lipid synthesis
inhibitors (e.g., phosphorodithioates, thiocarbamates,
benzofuranes, chlorocarbonic acids), protoporphyrinogen oxidase
(PPO) inhibitors (e.g., diphenylethers, N-phenylphthalimides,
oxadiazoles, oxazolidinediones, phenylpyrazoles, pyrimidindiones,
thiadiazoles, triazolinones), carotenoid biosynthesis inhibitors
(e.g., clomazone, amitrole, aclonifen), phytoene desaturase (PDS)
inhibitors (e.g., amides, anilidex, furanones, phenoxybutan-amides,
pyridiazinones, pyridines), 4-hydroxyphenyl-pyruvate-dioxygenase
(HPPD) inhibitors (e.g., callistemones, isoxazoles, pyrazoles,
triketones), cellulose biosynthesis inhibitors (e.g., nitriles,
benzamides, quinclorac, triazolocarboxamides), herbicides with
multiple modes-of-action such as quinclorac, and unclassified
herbicides such as arylaminopropionic acids, difenzoquat,
endothall, and organoarsenicals. Exemplary resistant or tolerant
weeds include, but are not limited to, biotypes with resistance or
tolerance to multiple herbicides, biotypes with resistance or
tolerance to multiple chemical classes, biotypes with resistance or
tolerance to multiple herbicide modes-of-action, and biotypes with
multiple resistance or tolerance mechanisms (e.g., target site
resistance or metabolic resistance).
[0428] By way of non-limiting illustration, examples of certain
embodiments of the present disclosure are given below.
EXAMPLES
Example 1. Herbicidal Activity and Effect on Crop Injury on Winter
Wheat of Compounds of Formula I and HPPD Herbicides in Greenhouse
Trials
Methodology--Evaluation of Postemergence Herbicidal Activity in
Crops
[0429] Seeds of the desired test plant species were planted in Sun
Gro MetroMix.RTM. 306 planting mixture, which typically has a pH of
6.0 to 6.8 and an organic matter content of about 30 percent, in
plastic pots with a surface area of 103.2 square centimeters
(cm.sup.2). When required to ensure good germination and healthy
plants, a fungicide treatment and/or other chemical or physical
treatment was applied. The plants were grown for 7-36 days (d) in a
greenhouse with an approximate 14-hour (h) photoperiod which was
maintained at about 23.degree. C. during the day and 22.degree. C.
during the night. Nutrients and water were added on a regular basis
and supplemental lighting was provided with overhead metal halide
1000-Watt lamps as necessary. The plants were employed for testing
when they reached the second or third true leaf stage.
[0430] The compound of Formula (1):
##STR00050##
was used with various HPPD inhibitors in herbicide evaluations.
[0431] An emulsifiable concentrate (EC) formulation containing
Compound 1 at 100 gai/L was prepared by combining Compound 1 with
1-butyl-2-pyrrolidinone (Tamisolve NxG; 360.5 g/L), benzyl acetate
(544.6 g/L) and Agnique MBL 520L surfactant (52.9 g/L). If Compound
1 did not dissolve readily, the mixture was warmed and/or
sonicated. The concentrated stock solutions were diluted with an
aqueous mixture of 1.5% v/v of Agri-dex crop oil concentrate to
provide the appropriate application rates. Compound requirements
are based upon a 12 milliliter (mL) application volume at a rate of
187 liters per hectare (L/ha). Spray solutions of the experimental
compound mixtures were prepared by adding the stock solutions to
the appropriate amount of dilution solution to form a 12 mL spray
solution in two-way combinations. Formulated compounds were applied
to the plant material with an overhead Mandel track sprayer
equipped with 8002E nozzles calibrated to deliver 187 L/ha over an
application area of 0.503 square meters (m.sup.2) at a spray height
of 18 inches (43 centimeters (cm)) above average plant canopy.
Control plants were sprayed in the same manner with the solvent
blank. Application rates for component (a) are in g ai/ha, and
application rates for component (b) are in g ai/ha.
[0432] The treated plants and control plants were placed in a
greenhouse as described above and watered by sub-irrigation to
prevent wash-off of the test compounds. After 20-22 d, the
condition of the test plants as compared with that of the control
plants was determined visually and scored on a scale of 0 to 100
percent where 0 corresponds to no injury and 100 corresponds to
complete kill. The condition of the test plants was compared with
that of the control plants as determined visually and scored on a
scale of 0 to 100 percent, where 0 corresponds to no injury and 100
corresponds to complete kill. The Colby method was used to
determine the herbicidal effects expected from the mixtures.
[0433] Compound 1 (formulated as an EC) was combined with
isoxaflutole and the efficacy of the herbicidal composition on
velvetleaf (Abutilon theophrasti, ABUTH), wild oat (Avena fatua,
AVEFA), winter rape (Brassica napus, BRSNW), thistle (Cirsium
arvense CIRAR), poinsettia (Euphorbia heterophylla, EPHHL), wild
buckwheat (Polygonum convolvulus, POLCO), grain sorghum (Sorghum
vulgare, SORVU), common chickweed (Stellaria media, STEME), wild
pansy (Viola tricolor, VIOTR), pigweed (Amaranthus retrollexus,
AMARE), common lambsquarters (Chenopodium album L., CHEAL), soybean
(Glycine max, GLXMA), sunflower (Helianthus annuus, HELAN), giant
foxtail (Setaria faberi, SETFA) spring rape (Brassica napus,
BRSNN), large crabgrass (Digitaria sanguinalis, DIGSA),
barnyardgrass (Echinochloa crus-galli, ECHCG), ivyleaf morningglory
(Ipomoea hederacea, IPOHE), kochia (Kochia scoparia, KCHSC), rice
(Oryza sativa, ORYSA), winter wheat (Triticum aestivum, TRZAW), and
maize (Zea mays, ZEAMX) were evaluated. The results are summarized
in Table 1 and include data averaged from two trials.
TABLE-US-00002 TABLE 1 Effect (% visual injury) of compound 1 and
isoxaflutole on weeds/crops. Compound 1 (g ai/ha) 5 10 0 5 10
Isoxaflutole (g ai/ha) Application Rate 0 0 35 35 35 ABUTH Obs 50
55 45 80 87 Exp 73 75 AVEFA Obs 0 0 60 60 65 Exp 60 60 BRSNW Obs 40
45 60 80 85 Exp 76 78 CIRAR Obs 50 60 75 100 97 Exp 88 90 EPHHL Obs
86 99 43 100 100 Exp 92 99 POLCO Obs 53 58 10 78 73 Exp 57 62 SORVU
Obs 0 50 0 85 93 Exp 0 50 STEME Obs 70 70 10 95 100 Exp 73 73 VIOTR
Obs 8 13 45 45 60 Exp 49 52 AMARE Obs 75 97 95 100 100 Exp 99 100
CHEAL Obs 90 98 99 100 100 Exp 100 100 GLXMA Obs 95 100 75 100 100
Exp 99 100 HELAN Obs 90 90 90 95 100 Exp 99 99 SETFA Obs 30 63 97
100 100 Exp 98 99 BRSNN Obs 50 80 85 85 97 Exp 93 97 DIGSA Obs 0 10
50 20 20 Exp 50 55 ECHCG Obs 20 60 25 30 50 Exp 40 70 IPOHE Obs 10
10 70 30 30 Exp 73 73 KCHSC Obs 63 68 90 93 95 Exp 96 97 ORYSA Obs
0 10 30 25 35 Exp 30 37 TRZAW Obs 0 0 15 20 30 Exp 15 15 ZEAMX Obs
0 0 0 10 20 Exp 0 0 g ai/ha = grams active ingredient per hectare
ABUTH = Abutilon theophrasti (velvetleaf) AVEFA = Avena fatua
(giant foxtail) BRSNW = Brassica napus (winter rape) CIRAR =
Cirsium arvense (thistle) EPHHL = Euphorbia heterophylla
(poinsettia) POLCO = Polygonum convolvulus (wild buckwheat) SORVU =
Sorghum vulgare (grain sorghum) STEME = Stellaria media (chickweed)
VIOTR = Viola tricolor (wild pansy) AMARE = Amaranthus retroflexus
(pigweed) CHEAL = Chenopodium album L. (common lambsquarters) GLXMA
= Glycine max (soybean) HELAN = Helianthus annuus (sunflower) SETFA
= Setaria faberi (giant foxtail) BRSNN = Brassica napus (spring
rape) DIGSA = Digitaria sanguinalis (large crabgrass) ECHCG =
Echinochloa crus-galli (barnyardgrass) IPOHE = Ipomoea hederacea
(ivyleaf morningglory) KCHSC = Kochia scoparia (kochia) ORYSA =
Oryza sativa (rice) TRZAW = Triticum aestivum (winter wheat)
[0434] Compound 1 (formulated as an EC) was combined with
mesotrione and the efficacy of the herbicidal composition on
velvetleaf (Abutilon theophrasti, ABUTH), pigweed (Amaranthus
retroflexus, AMARE), winter rape (Brassica napus, BRSNW),
barnyardgrass (Echinochloa crus-galli, ECHCG), poinsettia
(Euphorbia heterophylla, EPHHL), ivyleaf morningglory (Ipomoea
hederacea, IPOHE), wild buckwheat (Polygonum convolvulus, POLCO),
common chickweed (Stellaria media, STEME), wild pansy (Viola
tricolor, VIOTR), common lambsquarters (Chenopodium album L.,
CHEAL), thistle (Cirsium arvense CIRAR), soybean (Glycine max,
GLXMA), sunflower (Helianthus annuus, HELAN), spring rape (Brassica
napus, BRSNN), large crabgrass (Digitaria sanguinalis, DIGSA),
kochia (Kochia scoparia, KCHSC), giant foxtail (Setaria faberi,
SETFA), grain sorghum (Sorghum vulgare, SORVU), and maize (Zea
mays, ZEAMX) was evaluated. The results are summarized in Table 2
and include data averaged from two trials.
TABLE-US-00003 TABLE 2 Effect (% visual injury) of compound 1 and
mesotrione on weeds/crops. Compound 1 (g ai/ha) 5 10 0 5 10
Mesotrione (g ai/ha) Application Rate 0 0 35 35 35 ABUTH Obs 50 55
88 98 98 Exp 94 94 AMARE Obs 75 97 30 100 100 Exp 83 98 BRSNW Obs
40 45 60 85 85 Exp 76 78 ECHCG Obs 20 60 10 0 70 Exp 28 64 EPHHL
Obs 86 99 20 100 75 Exp 89 99 IPOHE Obs 10 10 70 93 95 Exp 73 73
POLCO Obs 53 58 48 100 100 Exp 75 78 STEME Obs 70 70 60 95 100 Exp
88 88 VIOTR Obs 8 13 58 73 88 Exp 61 63 CHEAL Obs 90 98 100 100 93
Exp 100 100 CIRAR Obs 50 60 100 100 100 Exp 100 100 GLXMA Obs 95
100 70 100 100 Exp 99 100 HELAN Obs 90 90 93 100 100 Exp 99 99
BRSNN Obs 50 80 100 95 100 Exp 100 100 DIGSA Obs 0 10 20 0 10 Exp
20 28 KCHSC Obs 63 68 70 80 80 Exp 89 90 SETFA Obs 30 63 0 5 65 Exp
30 63 SORVU Obs 0 50 0 0 30 Exp 0 50 ZEAMX Obs 0 0 0 0 0 Exp 0 0 g
ai/ha = grams active ingredient per hectare ABUTH = Abutilon
theophrasti (velvetleaf) AMARE = Amaranthus retroflexus (pigweed)
BRSNW = Brassica napus (winter rape) ECHCG = Echinochloa crus-galli
(barnyardgrass) EPHHL = Euphorbia heterophylla (poinsettia) IPOHE =
Ipomoea hederacea (ivyleaf morningglory) POLCO = Polygonum
convolvulus (wild buckwheat) STEME = Stellaria media (chickweed)
VIOTR = Viola tricolor (wild pansy) CHEAL = Chenopodium album L.
(common lambsquarters) CIRAR = Cirsium arvense (thistle) GLXMA =
Glycine max (soybean) HELAN = Helianthus annuus (sunflower) BRSNN =
Brassica napus (spring rape) DIGSA = Digitaria sanguinalis (large
crabgrass) KCHSC = Kochia scoparia (kochia) SETFA = Setaria faberi
(giant foxtail) SORVU = Sorghum vulgare (grain sorghum) ZEAMX = Zea
mays (maize)
[0435] Compound 1 (formulated as an EC) was combined with
sulcotrione and the efficacy of the herbicidal composition on
velvetleaf (Abutilon theophrasti, ABUTH), winter rape (Brassica
napus, BRSNW), poinsettia (Euphorbia heterophylla, EPHHL), ivyleaf
morningglory (Ipomoea hederacea, IPOHE), wild buckwheat (Polygonum
convolvulus, POLCO), grain sorghum (Sorghum vulgare, SORVU), common
chickweed (Stellaria media, STEME), pigweed (Amaranthus
retrollexus, AMARE), common lambsquarters (Chenopodium album L.,
CHEAL), thistle (Cirsium arvense CIRAR), barnyardgrass (Echinochloa
crus-galli, ECHCG), soybean (Glycine max, GLXMA), sunflower
(Helianthus annuus, HELAN), pansy (Viola tricolor, VIOTR), spring
rape (Brassica napus, BRSNN), kochia (Kochia scoparia, KCHSC), rice
(Oryza sativa, ORYSA), giant foxtail (Setaria faberi, SETFA),
winter wheat (Triticum aestivum, TRZAW), and maize (Zea mays,
ZEAMX) was evaluated. The results are summarized in Table 3 and
include data averaged from two trials.
TABLE-US-00004 TABLE 3 Effect (% visual injury) of compound 1 and
sulcotrione on weeds/crops. Compound 1 (g ai/ha) 5 10 0 5 10
Sulcotrione (g ai/ha) Application Rate 0 0 75 75 75 ABUTH Obs 50 55
50 95 98 Exp 75 78 BRSNW Obs 40 45 70 85 93 Exp 82 84 EPHHL Obs 86
99 60 100 100 Exp 94 99 IPOHE Obs 10 10 65 75 85 Exp 69 69 POLCO
Obs 53 58 48 83 99 Exp 75 78 SORVU Obs 0 50 0 40 40 Exp 0 50 STEME
Obs 70 70 85 100 100 Exp 96 96 AMARE Obs 75 97 40 85 100 Exp 85 98
CHEAL Obs 90 98 100 100 100 Exp 100 100 CIRAR Obs 50 60 70 85 93
Exp 85 88 ECHCG Obs 20 60 40 70 75 Exp 52 76 GLXMA Obs 95 100 65
100 100 Exp 98 100 HELAN Obs 90 90 80 100 100 Exp 98 98 VIOTR Obs 8
13 73 70 73 Exp 75 76 BRSNN Obs 50 80 95 85 83 Exp 98 99 KCHSC Obs
63 68 45 70 81 Exp 79 82 ORYSA Obs 0 10 5 10 20 Exp 5 15 SETFA Obs
30 63 0 10 30 Exp 30 63 TRZAW Obs 0 0 0 0 0 Exp 0 0 ZEAMX Obs 0 0 0
0 0 Exp 0 0 g ai/ha = grams active ingredient per hectare ABUTH =
Abutilon theophrasti (velvetleaf) BRSNW = Brassica napus (winter
rape) EPHHL = Euphorbia heterophylla (poinsettia) IPOHE = Ipomoea
hederacea (ivyleaf morningglory) POLCO = Polygonum convolvulus
(wild buckwheat) SORVU = Sorghum vulgare (grain sorghum) STEME =
Stellaria media (chickweed) AMARE = Amaranthus retrollexus
(pigweed) CHEAL = Chenopodium album L. (common lambsquarters) CIRAR
= Cirsium arvense (thistle) ECHCG = Echinochloa crus-galli
(barnyardgrass) GLXMA = Glycine max (soybean) HELAN = Helianthus
annuus (sunflower) VIOTR = Viola tricolor (wild pansy) BRSNN =
Brassica napus (spring rape) KCHSC = Kochia scoparia (kochia) ORYSA
= Oryza sativa (rice) SETFA = Setaria faberi (giant foxtail) TRZAW
= Trificum aestivum (winter wheat) ZEAMX = Zea mays (maize)
[0436] Compound 1 (formulated as an EC) was combined with
benzobicyclon and the efficacy of the herbicidal composition on
velvetleaf (Abutilon theophrasti, ABUTH), spring rape (Brassica
napus, BRSNN), thistle (Cirsium arvense CIRAR), poinsettia
(Euphorbia heterophylla, EPHHL), kochia (Kochia scoparia, KCHSC),
wild buckwheat (Polygonum convolvulus, POLCO), giant foxtail
(Setaria faberi, SETFA), wild pansy (Viola tricolor, VIOTR), and
common lambsquarters (Chenopodium album L., CHEAL) was evaluated.
The results are summarized in Table 4.
TABLE-US-00005 TABLE 4 Effect (% visual injury) of compound 1 and
benzobicyclon on weeds/crops. Compound 1 (g ai/ha) 5 10 0 5 10
Benzobicyclon (g ai/ha) Application Rate 0 0 50 50 50 ABUTH Obs 50
50 25 65 70 Exp 63 63 BRSNN Obs 50 80 0 60 95 Exp 50 80 CIRAR Obs
50 60 20 70 75 Exp 60 68 EPHHL Obs 75 100 5 100 100 Exp 76 100
KCHSC Obs 65 75 10 70 87 Exp 69 78 POLCO Obs 40 40 0 65 80 Exp 40
40 SETFA Obs 50 75 0 60 75 Exp 50 75 VIOTR Obs 10 15 10 40 50 Exp
19 24 CHEAL Obs 90 95 100 100 100 Exp 100 100 g ai/ha = grams
active ingredient per hectare ABUTH = Abutilon theophrasti
(velvetleaf) BRSNN = Brassica napus (spring rape) CIRAR = Cirsium
arvense (thistle) EPHHL = Euphorbia heterophylla (poinsettia) KCHSC
= Kochia scoparia (kochia) POLCO = Polygonum convolvulus (wild
buckwheat) SETFA = Setaria faberi (giant foxtail) VIOTR = Viola
tricolor (wild pansy) CHEAL = Chenopodium album L. (common
lambsquarters)
[0437] Compound 1 (formulated as an EC) was combined with
pyrazolynate and the efficacy of the herbicidal composition on
poinsettia (Euphorbia heterophylla, EPHHL), wild buckwheat
(Polygonum convolvulus, POLCO), common lambsquarters (Chenopodium
album L., CHEAL), thistle (Cirsium arvense CIRAR), wild pansy
(Viola tricolor, VIOTR), velvetleaf (Abutilon theophrasti, ABUTH),
spring rape (Brassica napus, BRSNN), and kochia (Kochia scoparia,
KCHSC) was evaluated. The results are summarized in Table 5.
TABLE-US-00006 TABLE 5 Effect (% visual injury) of compound 1 and
pyrazolynate on weeds/crops. Compound 1 (g ai/ha) 5 10 0 5 10
Pyrazolynate (g ai/ha) Application Rate 0 0 225 225 225 EPHHL Obs
75 100 0 95 100 Exp 75 100 POLCO Obs 40 40 0 10 60 Exp 40 40 CHEAL
Obs 90 95 10 70 90 Exp 91 96 CIRAR Obs 50 60 0 50 25 Exp 50 60
VIOTR Obs 10 15 0 10 10 Exp 10 15 ABUTH Obs 50 50 0 20 30 Exp 50 50
BRSNN Obs 50 80 0 25 20 Exp 50 80 KCHSC Obs 65 75 0 30 60 Exp 65 75
g ai/ha = grams active ingredient per hectare EPHHL = Euphorbia
heterophylla (poinsettia) POLCO = Polygonum convolvulus (wild
buckwheat) CHEAL = Chenopodium album L. (common lambsquarters)
CIRAR = Cirsium arvense (thistle) VIOTR = Viola tricolor (wild
pansy) ABUTH = Abutilon theophrasti (velvetleaf) BRSNN = Brassica
napus (spring rape) KCHSC = Kochia scoparia (kochia)
[0438] The compositions and methods of the appended claims are not
limited in scope by the specific compositions and methods described
herein, which are intended as illustrations of a few aspects of the
claims and any compositions and methods that are functionally
equivalent are intended to fall within the scope of the claims.
Various modifications of the compositions and methods in addition
to those shown and described herein are intended to fall within the
scope of the appended claims. Further, while only certain
representative compositions and method steps disclosed herein are
specifically described, other combinations of the compositions and
method steps also are intended to fall within the scope of the
appended claims, even if not specifically recited. Thus, a
combination of steps, elements, components, or constituents may be
explicitly mentioned herein or less, however, other combinations of
steps, elements, components, and constituents are included, even
though not explicitly stated. The term "comprising" and variations
thereof as used herein is used synonymously with the term
"including", "containing", and variations thereof and are open,
non-limiting terms. Although the terms "comprising" and "including"
have been used herein to describe various embodiments, the terms
"consisting essentially of" and "consisting of" can be used in
place of "comprising" and "including" to provide for more specific
embodiments of the invention and are also disclosed. Other than in
the examples, or where otherwise noted, all numbers expressing
quantities of ingredients, reaction conditions, and so forth used
in the specification and claims are to be understood at the very
least, and not as an attempt to limit the application of the
doctrine of equivalents to the scope of the claims, to be construed
in light of the number of significant digits and ordinary rounding
approaches.
* * * * *